Water → 2-(4-Benzyloxy-phenyl)-ethylamine

HRID 1459137Notes

Reaction equation

HRID 1459137 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N+:7]([CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][CH:13]=1)([O-])=O.O.[OH-].[Na+]>C(OCC)C>[C:20]1([CH2:19][O:18][C:15]2[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][NH2:7])=[CH:17][CH:16]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 27378921-(2-Nitroethenyl)-4-(phenylmethoxy)benzeneHCID 21226445Aluminium lithium hydride

Product 1

HCID 2009572-(4-Benzyloxy-phenyl)-ethylamineYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-(4-(Phenylmethoxy)phenyl)ethylamlne. Lithium aluminum hydride (8.48 g, 223 mmol) was suspended in dry diethyl ether (600 mL). 1-(2-Nitroethenyl)-4-(phenylmethoxy)benzene (13.9 g, 55 mmol) was extracted into this mixture using a Soxhlet apparatus. The mixture was boiled under reflux for 16 h. Water (7.38 mL) was added, followed by aqueous sodium hydroxide (20%; 5.53 mL) and water (27.8 mL). The suspension was filtered. The solvent was evaporated from the filtrate under reduced pressure to give 2-(4-(phenylmethoxy)phenyl)ethylamine (11.25 g, 91%).

Workup

  1. temperatureunder reflux for 16 h
  2. filtrationThe suspension was filtered
  3. customThe solvent was evaporated from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-618575903fcf4e67844ac25032404b9e
Source dataset
uspto-grants-1998_12
Patent number
US05853713

Reaction notes

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