Triethylamine → Ethyl 2-(1-methyl-4-(3-(4-octylphenyl)ureido)piperidin-4-yl)acetate

HRID 1192886노트

반응식

HRID 1192886 반응식
[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.[N:22]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:27][CH:26]=1)=[C:23]=[O:24]>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][C:23]([NH:22][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:27][CH:26]=2)=[O:24])[CH2:7][CH2:6]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 37026561-Isocyanato-4-octylbenzeneHCID 66865496Ethyl 2-(4-amino-1-methylpiperidin-4-yl)acetate

생성물 1

HCID 66865126Ethyl 2-(1-methyl-4-(3-(4-octylphenyl)ureido)piperidin-4-yl)acetate수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A stirred solution of ethyl 2-(4-amino-1-methylpiperidin-4-yl)acetate (62 mg, 0.308 mmol) in CH2Cl2 (2 mL) was treated with NEt3 (0.13 mL, 0.924 mmol.), and 1-isocyanato-4-octylbenzene (0.071 mL, 0.308 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 (94 mg, 71%). 1H NMR (400 MHz, CDCl3) δ 7.19 (d, 2H, J=8.4 Hz), 7.12 (d, 2H, J=8.4 Hz), 6.45 (bs, 1H), 4.78 (bs, 1H), 4.09 (q, 2H, J=7.2 Hz), 2.90 (s, 2H), 2.58-2.48 (m, 4H), 2.39-2.19 (m, 4H), 2.25 (s, 3H), 1.75-1.70 (m, 2H), 1.60-1.54 (m, 2H), 1.30-1.23 (m, 13H), 0.80 (t, 3H, 6.4 Hz); MS ESI 432.4 [M+H]+, calcd for [C25H41N3O3+H]+ 432.62.

후처리

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

출처 및 근거

ORD 기록
ord-0d9e2f454c2c473493096f03902a3b0f
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680282B2

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