Benzoyl chloride → HCID 20468369, compound

HRID 1903273Notes

Reaction equation

HRID 1903273 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([Cl:13])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:14]1([C:20]23[CH2:25][CH:24]2[CH2:23][NH:22][CH2:21]3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[ClH:13].[C:20]12([C:14]3[CH:15]=[CH:16][C:17]([C:5](=[O:12])[C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=4)=[CH:18][CH:19]=3)[CH2:25][CH:24]1[CH2:23][NH:22][CH2:21]2

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 101300941-Phenyl-3-azabicyclo[3.1.0]hexane

Product 1

HCID 20468369HCID 20468369, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 12.9 g. of aluminum chloride and 9.7 g. of benzoyl chloride in 55 ml. of dichloromethane is stirred at -10° C. To this is added 5.6 g. of 1-phenyl-3-azabicyclo[3.1.0]hexane over a period of 10 minutes while the temperature is maintained at -10° C. to -5° C. The reaction is then stirred at 0° C. for 10 minutes, and then at room temperature for two days. The mixture is carefully poured onto ice and then extracted with dichloromethane. The extract is dried, filtered, and then concentrated to 25 ml. and diluted with ether. The resultant solid is collected, washed with ether, dried and recrystallized from acetonitrile to give 2.0 g. of the desired product, m.p. 171°-173° C.

Workup

  1. additionA mixture of 12.9 g
  2. additionTo this is added 5.6 g
  3. waitat room temperature for two days
  4. additionThe mixture is carefully poured onto ice
  5. extractionextracted with dichloromethane
  6. customThe extract is dried
  7. filtrationfiltered
  8. concentrationconcentrated to 25 ml
  9. additionand diluted with ether
  10. customThe resultant solid is collected
  11. washwashed with ether
  12. customdried
  13. customrecrystallized from acetonitrile
  14. customto give 2.0 g

Sources & evidence

ORD record
ord-922740fc029849d2806dfb6430200953
Source dataset
uspto-grants-1984_03
Patent number
US04435419

Reaction notes

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