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

HRID 2112062Notes

Reaction equation

HRID 2112062 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 61.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(4-Chlorophenyl)-N-heptylacetamide (1.045 g, 3.902 mmol) was dissolved in THF (10 ml) and was cooled to 0° C. under argon atmosphere. (Methylthio)methane compound with borane (1:1) (0.741 g, 9.756 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 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 flashcromatography (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 was 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. temperaturethe mixture was refluxed for 5 hours
  2. temperatureAfter the mixture was cooled to room temperature
  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 flashcromatography (
  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-57e358f6c40144f1aa4d6bd71a750f87
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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