Water → HCID 20298675, compound

HRID 263103Notes

Reaction equation

HRID 263103 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[C:5]([CH:19]=[N:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:4]=1.[BH4-].[Na+].O>CO>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[C:5]([CH2:19][NH:20][CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 20298673HCID 20298673, compound

Product 1

HCID 20298675HCID 20298675, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

A stirred solution of 4-[3-[4-methoxy-2-[[(2-phenylethyl)imino]methyl]phenoxy]propyl]morpholine (41.7 g) in 190 ml of methanol is reduced with 12.4 g of sodium borohydride (added portionwise). A cold water bath is used to maintain the temperature of the reaction mixture at 35° C. After 3 hours, the solvent is treated with water and the product is extracted two times with ether. The ether fractions are combined, treated with water, dried and concentrated to give 33.3 g of the title compound, boiling point 249°-254° C. at 0.3-0.4 mm of Hg.

Workup

  1. additionadded portionwise)
  2. customA cold water bath is used
  3. extractionthe product is extracted two times with ether
  4. additiontreated with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fe8348d129434f4cae59d7cde03a901c
Source dataset
uspto-grants-1979_05
Patent number
US04156079

Reaction notes

Loading…