Dimethylformamide → 4-Amino-N-[1-(2-hydroxyethyl)-4-piperidinyl]-3-methoxybenzamide

HRID 1676523노트

반응식

HRID 1676523 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][OH:10])[CH2:4][CH2:3]1.N1([O:20][C:21](=O)[C:22]2[CH:27]=[CH:26][C:25]([NH2:28])=[C:24]([O:29][CH3:30])[CH:23]=2)C2C=CC=CC=2N=N1.CN(C)C=O.C(N(CC)CC)C>ClCCl>[NH2:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][OH:10])[CH2:4][CH2:3]2)=[O:20])=[CH:23][C:24]=1[O:29][CH3:30]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 106606854-Amino-3-methoxy-benzoic acid benzotriazol-1-yl esterHCID 157334452-(4-Aminopiperidin-1-yl)ethan-1-ol

생성물 1

HCID 580150034-Amino-N-[1-(2-hydroxyethyl)-4-piperidinyl]-3-methoxybenzamide수율 36.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of 0.70 g (3.23 mmole) of 2-(4-amino-piperidin-1-yl)-ethanol, 0.92 g of 4-amino-3-methoxy-benzoic acid benzotriazol-1-yl ester, and 5 mL of dimethylformamide was added 1.63 g (16.1 mmole) of triethylamine. The mixture was stirred overnight, then taken up in 150 mL of dichloromethane and washed twice with saturated aqueous sodium bicarbonate, once with water, once with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with dichloromethane-methanol (gradient, 100:0-80:20) to give 0.35 g of 4-amino-N-[1-(2-hydroxy-ethyl)-piperidin-4-yl]-3-methoxy-benzamide.

후처리

  1. washwashed twice with saturated aqueous sodium bicarbonate, once with water, once with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with dichloromethane-methanol (gradient, 100:0-80:20)

출처 및 근거

ORD 기록
ord-56297c28c7b841c1ac7832fa7136d6c0
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003785B2

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