Water → (2-(Benzyloxy)phenyl)methanamine

HRID 4534Notes

Reaction equation

HRID 4534 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([NH2:19])=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>CCOCC>[CH2:7]([O:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH2:17][NH2:19])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 2960512-(Benzyloxy)benzamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 13754432(2-(Benzyloxy)phenyl)methanamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a Soxhlet apparatus 18.4 g of lithium aluminium hydride in 1800 ml of dry ether are boiled under a nitrogen atmosphere at a bath temperature of 70°, 5.3 g of 2-benzyloxybenzamide being introduced into the Soxhlet thimble. After 21 hours the reaction mixture is immersed in an ice bath, and 18.4 ml of water, 18.4 ml of 15% sodium hydroxide solution and 55 ml of water are added dropwise in succession, whilst stirring. The temperature may be allowed to rise to a maximum of +10°. Stirring of the mixture is then continued at 20° and the resulting precipitate is suction-filtered and washed with ether. The filtrate is concentrated by evaporation in vacuo and the oil remaining is stirred with 500 ml of 10% hydrochloric acid and 400 ml of ether for 2 hours, whilst cooling with ice. The precipitated 2-benzyloxybenzylamine hydrochloride is suction-filtered, washed with water and ether and dried in vacuo. Melting point 190°-191°.

Workup

  1. customto rise to a maximum of +10°
  2. stirringStirring of the mixture
  3. customis then continued at 20°
  4. filtrationthe resulting precipitate is suction-filtered
  5. washwashed with ether
  6. concentrationThe filtrate is concentrated by evaporation in vacuo
  7. stirringthe oil remaining is stirred with 500 ml of 10% hydrochloric acid and 400 ml of ether for 2 hours
  8. temperaturewhilst cooling with ice
  9. filtrationThe precipitated 2-benzyloxybenzylamine hydrochloride is suction-filtered
  10. washwashed with water and ether
  11. customdried in vacuo

Sources & evidence

ORD record
ord-da6fedaf49bb44f0a01d1ff0ecf5e09e
Source dataset
uspto-grants-1988_02
Patent number
US04727067

Reaction notes

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