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

HRID 1731838Notes

Reaction equation

HRID 1731838 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-abe5a0a39ea04013bb2d3a2d3bd39f67
Source dataset
uspto-grants-1986_11
Patent number
US04623662

Reaction notes

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