Sodium borohydride → HCID 12711983, compound

HRID 1902859Notes

Reaction equation

HRID 1902859 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[BH4-].[Na+]>C(O)(C)C>[CH3:1][N:2]([CH3:17])[C:3]1([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 125956504-(4-Chlorophenyl)-4-(dimethylamino)cyclohexan-1-one

Product 1

HCID 12711983HCID 12711983, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 4.0 g. (0.016 mole) of 4-dimethylamino-4-(p-chlorophenyl)cyclohexanone in 60 ml. 95% isopropanol is warmed to dissolve the solid. Sodium borohydride (0.61 g.) is then added and the mixture stirred at room temperature for six hours. The bulk of the solvent is then removed in vacuum. The residue is taken up in water and methylene chloride. The organic layer is washed with water and brine and taken to dryness. The residual solid is recrystallized twice from acetone to afford 1.21 g. (30%) of product, melting point 148°-150.5° C.

Workup

  1. additionA suspension of 4.0 g
  2. dissolutionto dissolve the solid
  3. customThe bulk of the solvent is then removed in vacuum
  4. washThe organic layer is washed with water and brine
  5. customThe residual solid is recrystallized twice from acetone
  6. customto afford 1.21 g

Sources & evidence

ORD record
ord-79875edb40054933a5f91040e9a70b72
Source dataset
uspto-grants-1982_12
Patent number
US04366172

Reaction notes

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