Hydrochloric Acid → 2-Methyl-1-(p-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride

HRID 2049005Notes

Reaction equation

HRID 2049005 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([C:7]23[CH2:12][CH:11]2[CH2:10][NH:9][C:8]3=O)=[CH:3][CH:2]=1.[CH3:15][Li].[BH4-].[Na+].[ClH:19]>CCOCC.CO>[ClH:19].[CH3:15][CH:8]1[NH:9][CH2:10][CH:11]2[C:7]1([C:4]1[CH:5]=[CH:6][C:1]([CH3:14])=[CH:2][CH:3]=1)[CH2:12]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 128913851-(p-Tolyl)-3-azabicyclo[3.1.0]hexan-2-oneHCID 178418348HCID 178418348, compound

Product 1

HCID 233323662-Methyl-1-(p-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Using the method of M. Takeda, et al., Chem. Pharm. Bull., 24, 2312 (1976), 1-(p-tolyl)-3-azabicyclo[3.1.0]hexan-2-one is reacted with methyllithium followed by sodium borohydride. Excess reagents are decomposed with methanol, followed by 1 N hydrochloric acid, and then 1 N sodium hydroxide and then evaporation of the solution gives a residue which is dissolved in ether. This solution is dried over sodium sulfate and filtered, and to the filtrate is added dry hydrogen chloride. Filtration of this suspension gives 2-methyl-1-(p-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride.

Workup

  1. custom1 N sodium hydroxide and then evaporation of the solution
  2. customgives a residue which
  3. dry with materialThis solution is dried over sodium sulfate
  4. filtrationfiltered
  5. additionto the filtrate is added dry hydrogen chloride
  6. filtrationFiltration of this suspension

Sources & evidence

ORD record
ord-31ac89073c614fa1a877f8f75afc8f43
Source dataset
uspto-grants-1980_04
Patent number
US04196120

Reaction notes

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