1-Heptanamine → 2-(4-chlorophenyl)-N-heptylacetamide

HRID 2112061Notes

Reaction equation

HRID 2112061 reaction equation
[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(N(C(C)C)C(C)C)C1C=CC=CC=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](Cl)=[O:32])=[CH:26][CH:25]=1>C1COCC1>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([NH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:32])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 81271-HeptanamineHCID 906924-Chlorophenylacetyl chlorideHCID 4578032Benzyldiisopropylamine

Product 1

HCID 36599732-(4-chlorophenyl)-N-heptylacetamideYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Heptan-1-amine (1 g, 8.679 mmol) was dissolved in dry THF under N2 and polymer supported N-benzyl-N,N-diisopropylamine (4.955 g, 26.038 mmol) was added. The mixture was stirred for 30 min and cooled to 0° C. and (4-chlorophenyl)acetyl chloride (1.969 g, 10.415 mmol) was added. The solution was stirred overnight at room temperature. The excess of (4-chlorophenyl)acetyl chloride was removed by filtering the mixture through an NH2 cartridge. The solvent was removed by evaporation. The crude was purified by preparative HPLC (started with isocratic acetonitrile/buffer 60/40 and then the acetonitrile concentration was increased to 100%, the buffer was a mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min). The product containing fractions were pooled and the acetonitrile was removed by evaporation. EtOAc (10 ml) was added and the organic phase was washed with two portions of brine and dried (MgSO4) and the solvent was removed by evaporation to give 1.045 g of 2-(4-chlorophenyl)-N-heptylacetamide (yield 45.0%).

Workup

  1. additionwas added
  2. stirringThe solution was stirred overnight at room temperature
  3. customThe excess of (4-chlorophenyl)acetyl chloride was removed
  4. filtrationby filtering the mixture through an NH2 cartridge
  5. customThe solvent was removed by evaporation
  6. customThe crude was purified by preparative HPLC (
  7. concentrationthe acetonitrile concentration
  8. temperaturewas increased to 100%
  9. additiona mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min)
  10. additionThe product containing fractions
  11. customthe acetonitrile was removed by evaporation
  12. additionEtOAc (10 ml) was added
  13. washthe organic phase was washed with two portions of brine
  14. dry with materialdried (MgSO4)
  15. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-2303dcf5e85049a6bc0020c2132182bf
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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