N-butyl-4-chlorobenzamide → n-Butyl-4-chlorobenzenemethanamine

HRID 21378

Reaction equation

HRID 21378 reaction equation
C([NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)CCC.[H]1[BH2][H][BH2]1.Cl.O>C1COCC1>[CH2:6]([C:12]1[CH:11]=[C:10]([Cl:13])[CH:9]=[CH:8][C:7]=1[CH2:6][NH2:5])[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 346664N-butyl-4-chlorobenzamideHCID 21885828Hydrate;hydrochloride

Product 1

HCID 57375995n-Butyl-4-chlorobenzenemethanamineYield 164.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-butyl-4-chlorobenzamide (2.26 g; 0.011 mol) in dry THF (25 ml) was added slowly to an ice-cooled solution of 1.0M B2H6 --THF complex (45 ml; 0.045 tool) under a nitrogen blanket. When addition was complete, the mixture was stirred and heated to reflux for 3 hours, cooled and decomposed by dropwise addition of 1:1 conc aq HCl-water (10 ml). The mixture was then evaporated on a rotary evaporator at 60° for 1/2 hour to decompose the boron-amine complexes. The residue was taken up in water, strongly basified with aq NaOH and extracted with CH2Cl2 (3×25 ml). The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to give n-butyl-4-chlorobenzenemethanamine (1.79 g) as an oil. The oil was converted to the hydrochloride salt of the title compound (1.98 g) by crystallising from ethanolic HCl and ethyl acetate, mp 250°-252° after melting and resolidifying at 203°-207° .

Workup

  1. additionWhen addition
  2. temperatureheated
  3. temperatureto reflux for 3 hours
  4. temperaturecooled
  5. customThe mixture was then evaporated on a rotary evaporator at 60° for 1/2 hour
  6. extractionextracted with CH2Cl2 (3×25 ml)
  7. washThe combined extracts were washed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-78f7e330337c40a8bdfa74f1db69078a
Source dataset
uspto-grants-1995_06
Patent number
US05422355

Linked notes

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