Hydrochloric Acid → n,n-Dimethyl-3-azabicyclo[3.1.0]hexan-1-amine dihydrochloride

HRID 1366546Notes

Reaction equation

HRID 1366546 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]12[CH2:8][CH:7]1[CH2:6][N:5](CC1C=CC=CC=1)[CH2:4]2.[ClH:17]>CO.[Pd]>[ClH:17].[ClH:17].[CH3:1][N:2]([CH3:16])[C:3]12[CH2:8][CH:7]1[CH2:6][NH:5][CH2:4]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66936186racemic N,N-dimethyl-3-(phenylmethyl)-3-azabicyclo[3.1.0]hexan-1-amine

Product 1

HCID 66936286n,n-Dimethyl-3-azabicyclo[3.1.0]hexan-1-amine dihydrochlorideYield 102.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of racemic N,N-dimethyl-3-(phenylmethyl)-3-azabicyclo[3.1.0]hexan-1-amine (0.5800 g, 2.681 mmol) in MeOH (13 mL) was added 1 N aq. HCl (5.4 mL, 5.4 mmol) and 10% Pd/C (50% water, 120 mg). The mixture was hydrogenated under balloon pressure overnight, and then filtered. The solution was concentrated in vacuo and azeotroped with MeOH (4×50 mL) to give crude, racemic N,N-dimethyl-3-azabicyclo[3.1.0]hexan-1-amine dihydrochloride (0.5453 g, >100% crude yield) as a light yellow foam. LCMS: (M+H)+: 127.2.

Workup

  1. customwas hydrogenated under balloon pressure overnight
  2. filtrationfiltered
  3. concentrationThe solution was concentrated in vacuo
  4. customazeotroped with MeOH (4×50 mL)

Sources & evidence

ORD record
ord-1f16d1ba3f6b41cb8b35fc04ab148d64
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

Loading…