반응 #640196

반응 방정식

thianaphthene-2-carboxylic acid

oxalyl chloride

dimethylformamide

(±)-trans-1-(Benzo[b]thiophene-2-carbonyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)-ethyl-amide

→

Benzo[b]thiophene-2-carbonyl chloride

용매

methylene chloride

반응 조건

후처리

1. 1
   기타The crude 1-(benzo[b]thiophene-2-carbonyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)-ethyl-amide was isolated as a mixture of cis and trans isomers

실험 절차

(±)-trans-1-(Benzo[b]thiophene-2-carbonyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)-ethyl-amide was made following general procedure A, substituting benzo[b]thiophene-2-carbonyl chloride for 4-trifluoromethyl-benzoyl chlorided. Benzo[b]thiophene-2-carbonyl chloride was prepared by reaction of thianaphthene-2-carboxylic acid with oxalyl chloride and dimethylformamide in methylene chloride. The crude 1-(benzo[b]thiophene-2-carbonyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)-ethyl-amide was isolated as a mixture of cis and trans isomers. Purification by silica gel chromatography (1% methanol/methylene chloride) followed by purification via HPLC yielded (±)-trans-2-methyl-1-(pyrimidine-5-carbonyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)-ethyl-amide (34%). 1H-NMR (CDCl3) δ: 1.02-1.18 (m, 6H), 1.65-1.75 (m, 1H), 2.55-2.65 (m, 1H), 3.60-3.70 (m, 1H), 3.80 (q, 2H), 5.05-5.15 (m, 1H), 6.70 (d, 1H), 6.80-7.00 (m, 3H), 7.20-7.40 (m, 4H), 7.45 (s, 1H), 7.50 (d, 2H), 7.70 (d, 1H), 7.80 (d, 1H). MS m/z: 489/491 (M+1).

출처