I wonder in which country they speak Unavailable?
Probably German since they are from Univ. Tubingen, Germany.
Here is the full name for the journal
Hoppe-Seyler's Zeitschrift für physiologische Chemie
ISSN 0018-4888
Tyrosine Decarboxylation
Highly pure tyramine and its salts.
Patent DE2503315 (http://l2.espacenet.com/dips/viewer?PN=DE2503315&CY=gb&LG=en&DB=EPD)
Abstract
4-HOC6H4CH2CH2NH2 (I) was prepd. by the decarboxylation of (-)-tyrosine in boiling Ph2O, followed by treatment of the crude I with oxalic acid to give the oxalate salt (71%). A suspension of I oxalate in EtOH was treated wih gaseous HCl to give I.HCl. (I think it says 2 hours at 250-260C is all it takes, A german speaker can verify)
Decarboxylation of amino acids with formation of the corresponding amines and the preparation of the enol form of 2,5-diketopiperazines.
Abderhalden, Emil; Gebelein, Fritz.
Z. physiol. Chem. (1926), 152 125-31.
Journal written in Unavailable.
CAN 20:13073 AN 1926:13073
Abstract
Tyramine may be obtained in 95% yield by heating tyrosine to 240° with 20 parts of Ph2NH and extg. the latter with Et2O. Glycine and alanine yield MeNH2 and EtNH2, resp. dl-Leucylglycine under the same treatment gave 93% of the enol form of leucylglycine anhydride. a-Bromoisobutyryl-a-aminoisobutyric acid, m. 169°, was prepd. in 80% yield from Me2CBrCOBr and Me2C(NH2)CO2H. On treatment with 25% NH4OH this yielded a-aminoisobutyryl-a-aminoisobutyric acid (I), m. 214-6°. I is theoretically incapable of forming an enolic anhydride. When heated with Ph2NH it gave 89.7% of the keto form of the anhydride, which sublimes at 260°. dl-a-Aminobutyryl-dl-a-aminobutyric acid gave 98% of the enolic anhydride, m. 264°; dl-leucyl-dl-valine 90% of the enolic anhydride, m. 242°; dl-alanyl-dl-valine 96% of the anhydride, m. 262°; and dl-leucyl-dl-leucine 93.6% of the enolic anhydride, m. 266°.
Decarboxylation of amino acids. V. Formation of hordenine.
Kanao, Seizo; Suyama, Tadashi.
Yakugaku Zasshi (1967), 87(1), 99-100.
Journal written in Japanese. CAN 67:54410
Abstract
cf. CA 63: 7097f. N,N-Dimethyl-L-tyrosine (4.18 g.) is heated at 270° for 30 min. with 5 ml. Tetralin (contg. peroxide) and 50 g. Ph2NH under N atm., shaken with dil. HCl, cooled, filtered, and the filtrate evapd. to give 34.7% hordenine hydrochloride, m. 179° (EtOH); the free base (I) m. 119°; sulfate m. 207-8°. I (1.3 g.) in 40 ml. Et2O is treated with 1.5 g. p-O2NC6H4COCl under heating 30 min. to give 1.1 g. O-p-nitrobenzoylhordenine-HCl, m. 224°. Decarboxylation of 5.0 g. N,N-bis(carboxymethyl)tyramine using 6 ml. Tetralin (contg. peroxide) and 50 g. Ph2NH under heating also gives I.
Convenient synthesis of hordenine-2-14C.
Digenis, George A.; Burkett, J. W.; Mihranian, V.
Coll. Pharm., Univ. Kentucky, Lexington, Ky., USA.
J. Label. Compounds (1972), 8(2), 231-5.
Abstract
A simple and convenient lab. procedure for prepn. of hordenine, labeled at the carbon adjacent to the benzene ring, is described, by decarboxylation of tyrosine-3-14C and subsequent reductive methylation of the tyramine.
Those who give up essential liberties for temporary safety deserve neither liberty nor safety
PDF document: http://forkat.anorg.chemie.tu-muenchen.de/2/pdf/f2be00b5.pdf (http://forkat.anorg.chemie.tu-muenchen.de/2/pdf/f2be00b5.pdf)
The document describes the addition of secondary amines to benzyne, formed from aryl halides. The green-colored part above says "Two eqv of piperidine and one eqv of chlorobenzene in the prescense of 3 eqv of potassium tert-butoxide gives N-phenylpiperidine in 82% yield by heating in toluene at 135°C for 36h. Other solvents also works, o-xylene (79%), DME (72%), Dioxane (86%). DMSO gives only 57% as side-reactions also occur with that solvent." The references for these reactions are those in No 5 above.
They also say that 135°C is necessary, but that using even higher temps are unneccesary for good yields. In reference 6, more details regarding mono- and dialkylation of aniline can be found.
They also describe the addition of secondary amines to allylbenzene and styrene to give amphetamines/PEAs. That is described in detail in:
Tetrahedron 2000, 56, 5157-5162.
DOI:10.1016/S0040-4020(00)00436-1 (http://dx.doi.org/10.1016/S0040%2D4020%2800%2900436%2D1)
Post 465442 (https://www.thevespiary.org/talk/index.php?topic=7569.msg46544200#msg46544200)
(Rhodium: "Hydroamination Route to Amphetamines", Chemistry Discourse)
Alternative selective O-methylation for the compound in Post 285579 (https://www.thevespiary.org/talk/index.php?topic=6574.msg28557900#msg28557900)
(foxy2: "3,5-diiodo-4-methoxyphenethylamine", Chemistry Discourse)
Chemoselective O-methylation of N-acylated/sulfonylated tyrosine derivatives
Mireille Attolini, Thierry Boxus, Stéphane Biltresse and Jacqueline Marchand-Brynaert
Tetrahedron Letters 43(7), 1187-1188 (2002)
DOI:10.1016/S0040-4039(01)02349-8 (http://dx.doi.org/10.1016/S0040%2D4039%2801%2902349%2D8)
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)
Abstract
Methyl ethers of N-trifluoroacetyl- and N-(m-trifluoromethyl) phenylsulfonyl-6-nitro-tyrosine t-butyl ester were readily prepared by modified Mitsunobu reaction (DPPE, DIAD, MeOH). Williamson (MeI, K2CO3 or Li2CO3 or NaOH under phase transfer) and classical Mitsunobu conditions (PPh3, DEAD, MeOH) gave O,N-dimethylated derivatives as side or main products. O- versus N-selectivity in tyrosine methylation reactions depends on both pKa values and steric factors.