Hydrochloric Acid → 3,6-Dimethyl-1-phenyl-3-azabicyclo[3.1.0]hexane hydrochloride

HRID 66288Notes

Reaction equation

HRID 66288 reaction equation
[CH3:1][N:2]1[C:9](=O)[CH:6]2[CH:7]([CH3:8])[CH:5]2[C:3]1=O.[H-].COCCO[Al+]O[CH2:19][CH2:20]OC.[Na+].[H-].[OH-].[Na+].[ClH:27]>C1C=CC=CC=1>[ClH:27].[CH3:1][N:2]1[CH2:9][CH:6]2[C:5]([C:20]3[CH:19]=[CH:7][CH:6]=[CH:5][CH:3]=3)([CH:7]2[CH3:8])[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20468377N, 3-dimethylcyclopropane-1,2-dicarboximideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 204683953,6-Dimethyl-1-phenyl-3-azabicyclo[3.1.0]hexane hydrochloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of N, 3-dimethylcyclopropane-1,2-dicarboximide (U.S. Pat. No. 3,166,571, Ex. 2) in benzene is added sodium bis(2-methoxyethoxy)aluminum hydride (70% benzene solution) for several minutes. This solution is stirred at ambient temperature for several hours, refluxed for one hour, and then cooled and combined with sodium hydroxide and worked-up and converted to the hydrochloride as described in Example 11 to give the title product.

Workup

  1. temperaturerefluxed for one hour
  2. temperaturecooled

Sources & evidence

ORD record
ord-168ed15b30884ba8ad402f3096938736
Source dataset
uspto-grants-1978_12
Patent number
US04131611

Reaction notes

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