4-Chlorobenzoyl chloride → (4-Chlorophenyl)[1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]methanone

HRID 371941Notes

Reaction equation

HRID 371941 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:13][CH:12]2[CH2:11][NH:10][CH2:9]3)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>>[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([N:10]2[CH2:11][CH:12]3[C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)([CH2:13]3)[CH2:9]2)=[O:26])=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 10340Sodium CarbonateHCID 101303311-(4-Chlorophenyl)-3-azabicyclo[3.1.0]hexane

Product 1

HCID 20468348(4-Chlorophenyl)[1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]methanone

Procedure

Following the procedure of Example 8, 19.35 g. of 1-p-chlorophenyl-3-azabicyclo[3.1.0]hexane, 10.59 g. of sodium carbonate and 17.5 g. of p-chlorobenzoyl chloride are reacted. The benzene is evaporated and the dark purple residue is dissolved in 200 ml. of chloroform and washed successively with 5% sodium carbonate, 0.5N Hydrochloric acid and then with water and dried over sodium sulfate giving a dark purple oil. The oil is extracted with ether giving the product as grey crystals, mp 98°-100° C.

Workup

  1. customThe benzene is evaporated
  2. dissolutionthe dark purple residue is dissolved in 200 ml
  3. washof chloroform and washed successively with 5% sodium carbonate, 0.5N Hydrochloric acid
  4. dry with materialwith water and dried over sodium sulfate giving a dark purple oil
  5. extractionThe oil is extracted with ether giving the product as grey crystals, mp 98°-100° C.

Sources & evidence

ORD record
ord-5166335efd104c669893cdbd3d0243f6
Source dataset
uspto-grants-1978_05
Patent number
US04088652

Reaction notes

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