Methanol → 4-[4-(1-Methoxy-1,1'-bicyclohexan-4-yl)piperazinyl]benzoic acid ethyl ester

HRID 1816765ノート

反応式

HRID 1816765 の反応式
[N:1]1([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:18][O:19][C:20]1([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1.CO.C([BH3-])#N.[Na+]>C(O)(=O)C.O1CCCC1>[CH2:14]([O:13][C:11](=[O:12])[C:10]1[CH:9]=[CH:8][C:7]([N:1]2[CH2:2][CH2:3][N:4]([CH:23]3[CH2:24][CH2:25][C:20]([O:19][CH3:18])([CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[CH2:21][CH2:22]3)[CH2:5][CH2:6]2)=[CH:17][CH:16]=1)[CH3:15]

参加物

7

反応物 4

HCID 887MethanolHCID 2761178Ethyl 4-(piperazin-1-yl)benzoateHCID 5003444Sodium cyanoborohydrideHCID 224929241-Methoxy-1,1'-bicyclohexane-4-one

生成物 1

HCID 541335744-[4-(1-Methoxy-1,1'-bicyclohexan-4-yl)piperazinyl]benzoic acid ethyl ester収率 42.9%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To an ice cooled solution of ethyl 4-(piperazin-1-yl)benzoate (1.23 g) and 1-methoxy-1,1′-bicyclohexane-4-one (916 mg) in a mixed solvent of methanol (20 ml), tetrahydrofuran (15 ml) and acetic acid (0.74 ml) was added sodium cyanoborohydride (301 mg) in a stream of nitrogen. The mixture was stirred at this temperature for 1.5 hours and at room temperature for 7.5 hours. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate solution. Dichloromethane was added to the solution. The organic layer was taken, washed with sodium hydrogen carbonate solution and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (3:1 hexane-methanol elution) to give 4-[4-(1-methoxy-1,1′-bicyclohexan-4-yl)piperazinyl]benzoic acid ethyl ester (801 mg).

後処理

  1. customThe reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate solution
  2. additionDichloromethane was added to the solution
  3. washwashed with sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (3:1 hexane-methanol elution)

出典と根拠

ORDレコード
ord-e4a255101002494a8d0ec17fb2671aca
出典データセット
uspto-grants-2005_04
特許番号
US06884868B1

反応ノート

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