Hydrochloric Acid → Benzenemethanamine, N-butyl-2-chloro-

HRID 359980Notes

Reaction equation

HRID 359980 reaction equation
[CH2:1]([NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])[CH2:2][CH2:3][CH3:4].B.Cl>O1CCCC1>[CH2:1]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 347041N-butyl-2-chlorobenzamide

Product 1

HCID 485398Benzenemethanamine, N-butyl-2-chloro-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 21.2 g of N-(n-butyl)-2-chlorobenzamide in 100 ml of tetrahydrofuran was added with cooling to 200 ml of 1M borane in tetrahydrofuran and the mixture was stirred under reflux for 18 hours, allowed to cool, and treated with 6N hydrochloric acid. The organic solvent was evaporated, and the residue was partitioned between ether and aqueous sodium hydroxide solution. The ether layer was separated, dried, and evaporated. The residue was distilled to yield N-(n-butyl)-2-chlorobenzylamine as a colorless liquid, b.p. 65°-75° C. at 60μ.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureto cool
  3. customThe organic solvent was evaporated
  4. customthe residue was partitioned between ether and aqueous sodium hydroxide solution
  5. customThe ether layer was separated
  6. customdried
  7. customevaporated
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-b255bbb0034246bd89bf5b8e315a1036
Source dataset
uspto-grants-1991_03
Patent number
US05003106

Reaction notes

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