Cyclohexylamine → HCID 10469811, compound

HRID 1756019Notes

Reaction equation

HRID 1756019 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10](Cl)=[O:11]>C(Cl)(Cl)Cl>[CH:1]1([NH:7][C:10](=[O:11])[CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[Br:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 598182Bromophenylacetyl chloride

Product 1

HCID 10469811HCID 10469811, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of cyclohexylamine (10.9 g), triethylemine (11.1 g) and chloroform (200 ml), α-bromophenylacetyl chloride (23.3 g) was added dropwise over 10 minutes under cooling with ice and stirring, and the mixture was refluxed for 10 hours. After cooling by allowing to stand, the reaction mixture was washed with 0.5N hydrochloric acid (100 ml), with 0.5N aqueous solution of sodium hydroxide (100 ml) and with saturated saline solution (100 ml), and then concentrated. The residue was recrystallized from ethyl acetate-ethanol to obtain 12.2 g of title compound as colorless crystals. The mother liquor from recrystallization was concentrated and the residue was purified by means of column chromatography (developing solvent, chloroform:ethanol=20 : 1) to obtain 13.0 g of additional. title compound as colorless crystals (overall yield 85.4%).

Workup

  1. additionwas added dropwise over 10 minutes
  2. temperatureunder cooling with ice
  3. temperaturethe mixture was refluxed for 10 hours
  4. temperatureAfter cooling
  5. washthe reaction mixture was washed with 0.5N hydrochloric acid (100 ml), with 0.5N aqueous solution of sodium hydroxide (100 ml) and with saturated saline solution (100 ml)
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethyl acetate-ethanol

Sources & evidence

ORD record
ord-58c0bfa26a1e40f5a26d450545ae3635
Source dataset
uspto-grants-1995_08
Patent number
US05439919

Reaction notes

Loading…