Acetyl chloride → HCID 20468379, compound

HRID 1903271Notes

Reaction equation

HRID 1903271 reaction equation
Cl.[C:2]1([C:8]23[CH2:13][CH:12]2[CH2:11][NH:10][CH2:9]3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([Cl:17])(=[O:16])[CH3:15].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[ClH:17].[C:8]12([C:2]3[CH:3]=[CH:4][C:5]([C:14](=[O:16])[CH3:15])=[CH:6][CH:7]=3)[CH2:13][CH:12]1[CH2:11][NH:10][CH2:9]2

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 127198431-Phenyl-3-azabicyclo[3.1.0]hexane hydrochloride

Product 1

HCID 20468379HCID 20468379, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 3 g. portion of 1-phenyl-3-azabicyclo[3.1.0]hexane hydrochloride is added to a cold (0° C.) mixture of 2.8 g. of acetyl chloride and 6.9 g. of aluminum chloride in 30 ml. of dichloromethane, and the reaction is stirred for 15 minutes. The mixture is then brought to room temperature, stirred overnight and carefully poured onto ice. This mixture is extracted twice with dichloromethane, and the extracts are combined, dried, filtered and concentrated to an oil. This oil is dissolved in a minimum of dichloromethane and treated with an excess of ether to give a solid which is collected, washed with ether and dried. Recrystallization from acetonitrile gives 500 mg. of the desired product, m.p. 195°-197° C.

Workup

  1. customis then brought to room temperature
  2. additioncarefully poured onto ice
  3. extractionThis mixture is extracted twice with dichloromethane
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. dissolutionThis oil is dissolved in a minimum of dichloromethane
  8. additiontreated with an excess of ether
  9. customto give a solid which
  10. customis collected
  11. washwashed with ether
  12. customdried
  13. customRecrystallization from acetonitrile
  14. customgives 500 mg

Sources & evidence

ORD record
ord-7c717ac1d2904bd393aa4ccdd902f91e
Source dataset
uspto-grants-1984_03
Patent number
US04435419

Reaction notes

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