Benzaldehyde → HCID 13314306, compound

HRID 615312Notes

Reaction equation

HRID 615312 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[CH2:11][CH2:12][NH2:13].O>C1(C)C=CC=CC=1>[CH2:1]([NH:13][CH2:12][CH2:11][C:10]([OH:9])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 962Water2×HCID 13314305HCID 13314305, compound

Product 1

HCID 13314306HCID 13314306, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

34 g of benzaldehyde were added to a solution of 35 g (0.32 mole) of the 3-hydroxy-3-phenyl-4-(4-chlorophenoxy)-butylamine obtained as described in (b), in 700 ml of toluene, and the mixture was boiled in a water separator until the water had been removed. The solution was evaporated down, the residue was dissolved in 500 ml of methanol, and 25 g of sodium borohydride were added a little at a time. The reaction mixture was evaporated down, 2N sodium hydroxide solution was added to the residue and the mixture was extracted with 3 times 200 ml of ether. The ether was removed, and the resulting residue was dissolved in isopropanol, from which it was obtained in crystalline form. 83 g (68%) of N-benzyl-3-hydroxy-3-phenyl-4-(4-chlorophenoxy)-butylamine of melting point 84°-85° C. were obtained.

Workup

  1. customobtained
  2. customhad been removed
  3. customThe solution was evaporated down
  4. dissolutionthe residue was dissolved in 500 ml of methanol
  5. addition25 g of sodium borohydride were added a little at a time
  6. customThe reaction mixture was evaporated down
  7. addition2N sodium hydroxide solution was added to the residue
  8. extractionthe mixture was extracted with 3 times 200 ml of ether
  9. customThe ether was removed
  10. dissolutionthe resulting residue was dissolved in isopropanol, from which it
  11. customwas obtained in crystalline form

Sources & evidence

ORD record
ord-88c5827c5c6f49b99bc200f9217964aa
Source dataset
uspto-grants-1985_02
Patent number
US04499087

Reaction notes

Loading…