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

HRID 1903252Notes

Reaction equation

HRID 1903252 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 stirred slurry of 61.2 g. of 1-phenyl-1,2-cyclopropanedicarboximide (U.S. Pat. No. 3,166,571, Ex. 8) in 2 liters of benzene is added 400 ml. of Vitride® under nitrogen. The mixture is stirred at room temperature for 2 hours, refluxed for 4 hours and then stirred at room temperature for 20 hours. A 400 ml. portion of 10 N sodium hydroxide is added cautiously with stirring. The organic layer is washed twice with dilute sodium hydroxide and then with water, dried over magnesium sulfate and evaporated to give an amber oil. This oil is dissolved in dilute hydrochloric acid, washed with ether, filtered and the filtrate made basic with sodium hydroxide. The basic filtrate is extracted with benzene, dried over magnesium sulfate, filtered and evaporated to give 1-phenyl-3-azabicyclo[3.1.0]hexane as an amber oil. 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 3-cyclopropylcarbonyl-1-phenyl-3-azabicyclo[3.1.0]hexane 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-9e214ed146804bee9add82de1019f702
Source dataset
uspto-grants-1984_03
Patent number
US04435419

Reaction notes

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