Sodium borohydride → N-[[2-[3-(Dimethylamino)propoxy]phenyl]methyl]benzeneethanamine

HRID 26955Notes

Reaction equation

HRID 26955 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=[N:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+]>CO>[CH3:23][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][NH:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20394044HCID 20394044, compound

Product 1

HCID 21322747N-[[2-[3-(Dimethylamino)propoxy]phenyl]methyl]benzeneethanamineYield 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

A stirred solution of 36.0 g of N-[[2-[3-(dimethylamino)propoxy]phenyl]methylene]benzeneethanamine in 200 ml of methanol is treated portionwise with 13.0 g of sodium borohydride. The temperature is maintained at 35° C. using a cold water bath. After 3 hours, the solvent is evaporated and the semi-solid residue is treated with 300 ml of water. The product is extracted twice with 100 ml portions of ether. The solvent fractions are combined, treated with water, dried and concentrated to give 33.8 g of an oily product. Distillation yields 19.9 g of the title compound, boiling point 165°-170° C. at 0.15 mm of Hg.

Workup

  1. customthe solvent is evaporated
  2. additionthe semi-solid residue is treated with 300 ml of water
  3. extractionThe product is extracted twice with 100 ml portions of ether
  4. additiontreated with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-de899461519f42b2a255f9fa3da00f86
Source dataset
uspto-grants-1979_04
Patent number
US04151354

Reaction notes

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