Water → HCID 9794654, compound

HRID 432873Notes

Reaction equation

HRID 432873 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][C:6]([CH3:9])=[CH:5][CH2:4]1.N1C=CC=CC=1.[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1.O>ClCCl.C(OCC)(=O)C>[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:2][CH:3]2[CH2:8][CH2:7][C:6]([CH3:9])=[CH:5][CH2:4]2)=[O:22])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 678794-Fluorobenzoyl chlorideHCID 22171686HCID 22171686, compound

Product 1

HCID 9794654HCID 9794654, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-amino-4-methylcyclohex-3-ene hydrochloride (0.103 g) in dichloromethane (5 ml) were added in turn pyridine (0.14 ml) and 4-fluorobenzoyl chloride (83 μl) at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 1 hour, which was taken up into a mixture of water and ethyl acetate. The separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate, and brine, and dried over magnesium sulfate. Evaporation under reduced pressure gave a residue, which was chromatographed on silica gel (50 ml) eluting with 0-20% ethyl acetate in n-hexane to give 1-(4-fluorobenzoylamino)-4-methylcyclohex-3-ene (98 mg).

Workup

  1. washThe separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate, and brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation under reduced pressure
  4. customgave a residue, which
  5. customwas chromatographed on silica gel (50 ml)
  6. washeluting with 0-20% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-72dedf54ecf246f0bdb3f350add1ce56
Source dataset
uspto-grants-2003_12
Patent number
US06664293B2

Reaction notes

Loading…