Electric Literature of 120157-97-3, The chemical industry reduces the impact on the environment during synthesis 120157-97-3, name is N-Boc-2-(4-Bromophenyl)ethylamine, I believe this compound will play a more active role in future production and life.
To a solution of 4-BROMOPHENETHYLAMINE (10G, 48. 98mmol) in anhydrous DMF (150mL), containing anhydrous triethylamine (35mL, 244.9 mol), was added BOC2O. The reaction mixture was heated for 15 minutes at 50C. After cooling to room temperature, brine (100ML) and HCI (1N, 100ML) were added subsequently, and the mixture was extracted several times with ether. The recombined organic layer was washed again with brine, dried over sodium sulfate, filtered and evaporated. The crude was flashed with 10% ethyl acetate in hexanes to give the [2- (4-BROMO-PHENYL)-ETHYL]-CARBAMIC acid tert-butyl ester.’H NMR (CDCI3, 300MHZ) : 1.41 (s, 9H); 2.22 (t, J=7. 1HZ, 2H); 3.31 (m, 2H); 4.67 (s, broad, 1 H); 7.03 (d, J=8.2Hz, 2H); 7.38 (d, J=8.2Hz, 2H). A mixture of the above mentioned compound (1. 00g, 3. 33MMOL), 3, 4-DIMETHOXYPHENYLBORONIC acid (1. 21 G, 6. 66MMOL), and potassium hydroxide (2N, 5mL, 10MMOL) in THF (15mL) was degassed using argon for 5 minutes. Palladium tetrakis-triphenylphosphine (200mg, 0. 167MMOL) was added and the mixture was heated at 85C. After 24 hours, the reaction mixture was allowed to cool to room temperature. Brine (20mL) was added and the reaction mixture was extracted several times with ether. The recombined organic phase was extracted with brine, dried over sodium sulfate, filtered, and evaporated. Silica gel chromatography of the crude using 20% ethyl acetate/n-hexane afforded [2- (3′, 4′-DIMETHOXY-BIPHENYL-4YL)-ETHYLAMINE]-CARBAMIC acid tert-butyl ester as a white SOLID. 1H-NMR (CDCI3, 300MHZ) : 1.44 (s, 9H); 2.82 (t, J=6.9Hz, 2H); 3.39 (m, 2H); 3.91 (s, 3H); 3.93 (s, 3H); 4.67 (s, broad, 1H) ; 6.92 (d, J=8.2Hz, 1 H) ; 7.11 (m, 2H); 7.25 (m, 2H); 7.48 (d, J=8. 1 Hz, 2H). A solution of the above mentioned compound (1.14g, 3. 19mmol) in anhydrous methanol (50mL) was cooled in ice bath and then treated drop wise with acetyl chloride. Stirring was continued for 30 minutes at the same temperature followed by overnight stirring at room temperature. About 30mL of the solvent was removed by evaporation and the mixture was diluted with 200mL of ether. The entitled product was collected as a white solid by filtration, followed by washing with anhydrous ether and drying under high VACUUM.’H-NMR (D20, 300MHZ) : 2.80 (t, J=6.9Hz, 2H); 3.40 (m, 2H); 3.91 (s, 3H); 3.93 (s, 3H); 4.77 (s, broad, 1H) ; 7.00 (d, J=8.2Hz, 1H) ; 7.15 (m, 2H); 7.26 (m, 2H); 7.50 (d, J=8. 1HZ, 2H)
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, N-Boc-2-(4-Bromophenyl)ethylamine, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; BIOMEP INC.; WO2004/50620; (2004); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics