Water → HCID 19801189, compound

HRID 1646618Notes

Reaction equation

HRID 1646618 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[CH:8]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:31][CH3:32])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])[CH2:7]2.[BH4-].[Na+].O>CO>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([OH:15])[CH:8]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:31][CH3:32])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])[CH2:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 19801190HCID 19801190, compound

Product 1

HCID 19801189HCID 19801189, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the 5,6-dimethoxy-2-[5-[N-ethyl-N-[(2-methoxyphenyl)methyl]amino]pentyl]-1-indanone hydrochloride (0.75 g) in methanol (10 ml) was gradually added sodium borohydride (0.3 g) and the mixture was stirred at room temperature for 6 hours. The excess sodium borohydride was then decomposed by addition of water and the solvent was distilled off under reduced pressure. The product was extracted into dichloromethane and washed with water. The dichloromethane layer was dried over anhydrous sodium sulfate and the solvent was distilled off to give 0.63 g of a colorless oil.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. extractionThe product was extracted into dichloromethane
  3. washwashed with water
  4. dry with materialThe dichloromethane layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-3e81e3cdf38e47a7bb684f68802166b6
Source dataset
uspto-grants-1993_01
Patent number
US05180746

Reaction notes

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