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

HRID 1676523ノート

反応式

HRID 1676523 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-56297c28c7b841c1ac7832fa7136d6c0
出典データセット
uspto-grants-2011_08
特許番号
US08003785B2

反応ノート

読み込み中…