Benzaldehyde → 4-amino-N-((1-(5-benzylaminopentyl)piperidin-4-yl)methyl)-5-chloro-2-methoxybenzamide

HRID 344393

반응식

HRID 344393 반응식
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[C:31]([Cl:32])=[CH:30][C:13]([C:14]([NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH2:29])[CH2:20][CH2:19]2)=[O:15])=[C:12]([O:33][CH3:34])[CH:11]=1.[BH4-].[Na+].O>C(O)C>[NH2:9][C:10]1[C:31]([Cl:32])=[CH:30][C:13]([C:14]([NH:16][CH2:17][CH:18]2[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:22][CH2:23]2)=[O:15])=[C:12]([O:33][CH3:34])[CH:11]=1

참가 물질

6

반응물 4

HCID 240BenzaldehydeHCID 962WaterHCID 4311764Sodium borohydrideHCID 540083634-Amino-N-(1-(5-aminopentyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

생성물 1

HCID 540154964-amino-N-((1-(5-benzylaminopentyl)piperidin-4-yl)methyl)-5-chloro-2-methoxybenzamide수율 72%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Benzaldehyde (0.76 g) was added to a solution of 4-amino-N-(1-(5-aminopentyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide (2.0 g) in ethanol (50 ml), and the mixture was stirred at refluxing temperature for 3 hr. Sodium borohydride (0.53 g) was added to the reaction mixture under ice-cooling, and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol:ammonia=50:5:1) to give 1.78 g of 4-amino-N-((1-(5-benzylaminopentyl)piperidin-4-yl)methyl)-5-chloro-2-methoxybenzamide.

후처리

  1. temperatureat refluxing temperature for 3 hr
  2. temperaturecooling
  3. stirringthe mixture was stirred overnight at room temperature
  4. extractionthe mixture was extracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol:ammonia=50:5:1)

출처 및 근거

ORD 기록
ord-d8d6108f1b35472588e42ea8e4f89e05
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05864039

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