Hydrochloric Acid → N-[2-(4-chlorophenyl)ethyl]-N-heptylamine

HRID 2112045Notes

Reaction equation

HRID 2112045 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=O)=[CH:4][CH:3]=1.B.CSC.Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 36599732-(4-chlorophenyl)-N-heptylacetamideHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 43130216N-[2-(4-chlorophenyl)ethyl]-N-heptylamineYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Chlorophenyl)-N-heptylacetamide (0.886 g, 3.797 mmol) was dissolved in THF (10 ml) and was cooled to zero degrees under argon atmosphere. (Methylthio)methane compound with borane (1:1) (0.741 g, 9.755 mmol) was added and the mixture was refluxed for 5 hours. After the mixture was cooled to room temperature, 5 ml HCl (10%) was gently added and the mixture was stirred overnight. The solvent was removed by evaporation. EtOAc (20 ml) was added and the organic phase was washed with K2CO3 (2M, 2×20 ml). The crude was purified by flash chromatography (started with isocratic heptane/EtOAc 50/50 and then the EtOAc concentration was increased to 100%, (silica gel 60 0.004-0.063 mm). The product containing fractions were pooled and the EtOAc was removed by evaporation to give 0.609 g of N-[2-(4-chlorophenyl)ethyl]-N-heptylamine (yield 61.5%).

Workup

  1. temperaturewas cooled to zero degrees under argon atmosphere
  2. temperaturethe mixture was refluxed for 5 hours
  3. customThe solvent was removed by evaporation
  4. additionEtOAc (20 ml) was added
  5. washthe organic phase was washed with K2CO3 (2M, 2×20 ml)
  6. customThe crude was purified by flash chromatography (
  7. concentrationthe EtOAc concentration
  8. temperaturewas increased to 100%, (silica gel 60 0.004-0.063 mm)
  9. additionThe product containing fractions
  10. customthe EtOAc was removed by evaporation

Sources & evidence

ORD record
ord-2e7232bdd8ff48159e4c57389afeb2dd
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

Loading…