Hydrochloric Acid → N-(2-phenylethyl)heptan-1-amine

HRID 2112049Notes

Reaction equation

HRID 2112049 reaction equation
[CH2:1]([NH:8][C:9](=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].B.CSC.Cl>C1COCC1>[C:11]1([CH2:10][CH2:9][NH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5152095HCID 5152095, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 17206199N-(2-phenylethyl)heptan-1-amineYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Heptyl-2-phenylacetamide (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) (0.721 g, 9.492 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 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 0.584 g of N-(2-phenylethyl)heptan-1-amine (yield 70.1%).

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-740af7907d2245deaa93cd4bfd83a99e
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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