4-Butoxybenzaldehyde → HCID 59808329、化合物

HRID 563145ノート

反応式

HRID 563145 の反応式
Cl.[NH2:2][C@@H:3]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5].CCN(C(C)C)C(C)C.[CH2:35]([O:39][C:40]1[CH:47]=[CH:46][C:43]([CH:44]=O)=[CH:42][CH:41]=1)[CH2:36][CH2:37][CH3:38].[BH4-].[Na+]>CO.O>[CH2:12]([N:9]1[CH2:10][CH2:11][N:6]([C:4](=[O:5])[C@@H:3]([NH:2][CH2:44][C:43]2[CH:46]=[CH:47][C:40]([O:39][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:41][CH:42]=2)[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:7][CH2:8]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

7

反応物 4

HCID 798134-ButoxybenzaldehydeHCID 81531DiisopropylethylamineHCID 4311764Sodium borohydrideHCID 67005485HCID 67005485、化合物

生成物 1

HCID 59808329HCID 59808329、化合物収率 67.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

2-Amino-1-(4-benzyl-piperazin-1-yl)-(S)-3-phenyl-propan-1-one hydrochloride (500 mg, 1.26 mmol) were dissolved in MeOH (5 mL), DIPEA (359 mg, 2.77 mmol) and 4-n-butoxybenzaldehyde (226 mg, 1.26 mmol) was added and the mixture was heated to reflux for 2 h, cooled again to rt followed by slow addition of sodium borohydride (48 mg, 1.26 mmol) in portions. Stirring was continued for 15 min. Water (1 mL) was added and the solvents were removed under reduced pressure. The residue was taken up in diethylether (5 mL), washed with 10% aq. citric acid (5 mL) and water (5 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to give 411 mg (67%) of 1-(4-benzyl-piperazin-1-yl)-2-(4-butoxy-benzylamino)-(S)-3-phenyl-propan-1-one. LC-MS: tR=0.74 min; [M+H]+=486.43.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. customthe solvents were removed under reduced pressure
  4. washwashed with 10% aq. citric acid (5 mL) and water (5 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-edc50b27b88c4e86aea8c5d833b9b7b9
出典データセット
uspto-grants-2011_11
特許番号
US08067419B2

反応ノート

読み込み中…