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

HRID 1704681Notes

Reaction equation

HRID 1704681 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-130b0b119e1745cda68804c481d62ecc
Source dataset
uspto-grants-1978_11
Patent number
US04127606

Reaction notes

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