Sodium borohydride → 3-benzyl-7-piperazin-1-yl-1H-indole

HRID 18174Notes

Reaction equation

HRID 18174 reaction equation
[C:1]([C:9]1[C:17]2[C:12](=[C:13]([N:18]3[CH2:23][CH2:22][N:21](C(=O)C(F)(F)F)[CH2:20][CH2:19]3)[CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].CCOC(C)=O.O>C(O)(C)C>[CH2:1]([C:9]1[C:17]2[C:12](=[C:13]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 22728543Water ethylacetateHCID 593449261-[4-(3-Benzoyl-1H-indol-7-yl)-piperazin-1-yl]-2,2,2-trifluoro-ethanone

Product 1

HCID 593448843-benzyl-7-piperazin-1-yl-1H-indoleYield 126.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 1-[4-(3-benzoyl-1H-indol-7-yl)-piperazin-1-yl]-2,2,2-trifluoro-ethanone (638 mg, 1.59 mmol) in isopropanol (30 ml) was added NaBH4 (0.12 g, 3.17 mmol). After heating at reflux for 3 days, the reaction mixture was allowed to cool to room temperature and poured into a mixture of EtOAc/H2O. The organic layer was separated and washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo to give crude 3-benzyl-7-piperazin-1-yl-1H-indole as an oil (586 mg) which was used without further purification.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 3 days
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialAfter drying over MgSO4
  6. concentrationthe organic fraction was concentrated in vacuo

Sources & evidence

ORD record
ord-b543c4254c234e0e922351eb9356df5e
Source dataset
uspto-grants-2010_06
Patent number
US07741326B2

Reaction notes

Loading…