Sodium borohydride → 1-{[5-(1-Hydroxyethyl)-2-methoxy-4-methylphenyl]aminocarbonyl}-4-(3,5-dimethoxyphenyl)piperazine

HRID 377930Notes

Reaction equation

HRID 377930 reaction equation
[C:1]([C:4]1[C:5]([CH3:31])=[CH:6][C:7]([O:29][CH3:30])=[C:8]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C>[OH:3][CH:1]([C:4]1[C:5]([CH3:31])=[CH:6][C:7]([O:29][CH3:30])=[C:8]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 193571071-[(5-Acetyl-2-methoxy-4-methylphenyl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine

Product 1

HCID 193570541-{[5-(1-Hydroxyethyl)-2-methoxy-4-methylphenyl]aminocarbonyl}-4-(3,5-dimethoxyphenyl)piperazineYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[(5-Acetyl-2-methoxy-4-methylphenyl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine(0.2 g, 0.47 mmol) was dissolved in anhydrous ethanol(15 ml), and sodium borohydride(17 mg) was added thereto, and then the resulting mixture was stirred at room temperature for 2 hours, concentrated under the reduced pressure to remove ethanol, and purified by column chromatography(ethylacetate:hexane=1:2) to obtain the titled compound.

Workup

  1. concentrationconcentrated under the reduced pressure
  2. customto remove ethanol
  3. custompurified by column chromatography(ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-f71ce18fc9684c06a59b0bda559dfce8
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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