Triethylamine → Ethyl 2-(1-methyl-4-(4-pentylphenylsulfonamido)piperidin-4-yl)acetate

HRID 1192888ノート

反応式

HRID 1192888 の反応式
[NH2:1][C:2]1([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.CCN(CC)CC.[CH2:22]([C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1)[CH2:23][CH2:24][CH2:25][CH3:26]>C(Cl)Cl>[CH3:8][N:5]1[CH2:4][CH2:3][C:2]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([NH:1][S:33]([C:30]2[CH:31]=[CH:32][C:27]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:28][CH:29]=2)(=[O:35])=[O:34])[CH2:7][CH2:6]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 1446254-t-Amylbenzenesulphonyl chlorideHCID 66865496Ethyl 2-(4-amino-1-methylpiperidin-4-yl)acetate

生成物 1

HCID 66865313Ethyl 2-(1-methyl-4-(4-pentylphenylsulfonamido)piperidin-4-yl)acetate収率 95.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A stirred solution of ethyl 2-(4-amino-1-methylpiperidin-4-yl)acetate (76 mg, 0.378 mmol) in CH2Cl2 (2 mL) was treated with NEt3 (0.24 mL, 1.70 mmol), and 4-pentylbenzene-1-sulfonyl chloride (140 mg, 0.567 mmol). The reaction was stirred overnight, at room temperature, then the solvent removed in vacuo and the product purified by column chromatography to obtain the title compound (148 mg, 95%). 1H NMR (400 MHz, CD3OD) δ 7.77 (d, 2H, J=7.6 Hz), 7.35 (d, 2H, J=7.3 Hz), 4.00 (q, 2H, J=6.7), 2.69 (t, 2H, J=7.0 Hz), 2.57 (s, 2H), 2.46-2.36 (m, 2H), 2.20-2.02 (m, 7H), 1.68-1.60 (m, 4H), 1.41-1.25 (m, 4H), 1.20 (t, 3H, J=6.4 Hz), 0.89 (t, 3H, J=6.7 Hz); MS ESI 411.3 [M+H]+, calcd for [C21H34N2O4S+H]+ 411.58.

後処理

  1. customthe solvent removed in vacuo
  2. customthe product purified by column chromatography

出典と根拠

ORDレコード
ord-37f72cd679d742d6afcf979d1eb87889
出典データセット
uspto-grants-2014_03
特許番号
US08680282B2

反応ノート

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