Benzene → HCID 23332345, compound

HRID 371938Notes

Reaction equation

HRID 371938 reaction equation
[C:1]1([C:7]23[CH2:12][CH:11]2[CH2:10][NH:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[F:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30]>CCOCC.O>[F:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29]([N:9]1[CH2:10][CH:11]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([CH2:12]2)[CH2:8]1)=[O:30]

Participants

7

Reactant 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 743763-Fluorobenzoyl chlorideHCID 101300941-Phenyl-3-azabicyclo[3.1.0]hexane

Product 1

HCID 23332345HCID 23332345, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A 6.4 g. portion of 1-phenyl-3-azabicyclo[3.1.0]-hexane is added to 60 ml. of benzene. A 4.2 g. portion of sodium carbonate in 40 ml. of water is added with stirring. A 6.3 g. portion of m-fluorobenzoyl chloride is added and the mixture is stirred overnight. The oil present in the aqueous layer is extracted with chloroform, washed successively with water, dilute hydrochloric acid and water, dried over magnesium sulfate, filtered and evaporated giving an oil. This oil is dissolved in ether. A small amount of petroleum ether is added and the product is recovered as a white solid, mp 68°-69.5° C.

Workup

  1. stirringthe mixture is stirred overnight
  2. extractionThe oil present in the aqueous layer is extracted with chloroform
  3. washwashed successively with water, dilute hydrochloric acid and water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customgiving an oil
  8. customthe product is recovered as a white solid, mp 68°-69.5° C.

Sources & evidence

ORD record
ord-040b5bb71bb04318a0dea5195d6c3bb1
Source dataset
uspto-grants-1978_05
Patent number
US04088652

Reaction notes

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