2-(4-Chloro-phenyl)-N-ethyl-acetamide → [2-(4-Chloro-phenyl)-ethyl]-ethyl-amine hydrochloride

HRID 1866529Notes

Reaction equation

HRID 1866529 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH2:12][CH3:13])=O)=[CH:4][CH:3]=1>O1CCCC1.CO.Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][NH:11][CH2:12][CH3:13])=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 44191372-(4-Chloro-phenyl)-N-ethyl-acetamide

Product 1

HCID 69026677[2-(4-Chloro-phenyl)-ethyl]-ethyl-amine hydrochlorideYield 99%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-chloro-phenyl)-N-ethyl-acetamide (preparation 80), (437 mg, 2.22 mmol) and borane tetrahydrofuran complex (1M, 8.88 mL, 8.88 mmol) in tetrahydrofuran was heated under reflux for 18 hours. The cooled reaction mixture was then diluted with methanol (5 mL) and 12M hydrochloric acid (2 mL) and the re-heated to reflux for a further hour. The mixture was cooled to room temperature and concentrated in vacuo. Trituration of the residue with ethyl acetate afforded the title compound as a colourless solid in 99% yield, 403 mg.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customThe cooled reaction mixture
  4. temperaturethe re-heated
  5. temperatureto reflux for a further hour
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9498db197f2140f3872caad7c4f9cd19
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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