Benzene → 3-Cyclopropylcarbonyl-1-phenyl-3-azabicyclo[3.1.0]hexane

HRID 371932Notes

Reaction equation

HRID 371932 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(N(CC)CC)C.[CH:26]1([C:29](Cl)=[O:30])[CH2:28][CH2:27]1>O>[CH:26]1([C:29]([N:9]2[CH2:10][CH:11]3[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)([CH2:12]3)[CH2:8]2)=[O:30])[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 241Benzene2×HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 101300941-Phenyl-3-azabicyclo[3.1.0]hexane

Product 1

HCID 128913673-Cyclopropylcarbonyl-1-phenyl-3-azabicyclo[3.1.0]hexane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 15.9 g. of 1-phenyl-3-azabicyclo-[3.1.0]hexane in 100 ml. of benzene and 20 ml. of triethylamine is added 11.0 g. of cyclopropanecarboxylic acid chloride in 20 ml. of benzene over 5 minutes. The mixture is stirred for 30 minutes and 50 ml. of water is added. The benzene layer is extracted with dilute sodium bicarbonate followed by dilute hydrochloric acid and then water, dried over magnesium sulfate and evaporated to give the product as a brown oil.

Workup

  1. extractionThe benzene layer is extracted with dilute sodium bicarbonate
  2. dry with materialwater, dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-6c7e786f5e7246dd812b2581f5b5eec3
Source dataset
uspto-grants-1978_05
Patent number
US04088652

Reaction notes

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