Hydrochloric Acid → 4-Phenylbenzylamine

HRID 433121Notes

Reaction equation

HRID 433121 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B.Cl.[OH-].[Na+]>C1COCC1>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][NH2:13])=[CH:14][CH:15]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 14798Sodium HydroxideHCID 6025064-Phenylbenzamide

Product 1

HCID 3449894-PhenylbenzylamineYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, 4-phenylbenzamide (2.01 g, 10.2 mmol) was dissolved in THF (50 mL) and heated to reflux. To the mixture was added dropwise 1 M borane in THF (80.0 mL, 80.0 mmol). After refluxing for 18 h, the reaction mixture was cooled to room temperature and treated with 1 N HCl (40 mL). The solution was made basic via addition of 3 N NaOH (60 mL) and extracted with ethyl acetate (3×370 mL). The extract was washed with brine and dried over sodium sulfate. Concentration yielded 4-phenylbenzyl amine as a white solid (1.73 g, 93%).

Workup

  1. temperatureheated to reflux
  2. temperatureAfter refluxing for 18 h
  3. extractionextracted with ethyl acetate (3×370 mL)
  4. washThe extract was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationConcentration

Sources & evidence

ORD record
ord-615c0d892bcf459b9b47b2404f723b29
Source dataset
uspto-grants-2003_12
Patent number
US06667311B2

Reaction notes

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