(2R)-4-(1-(Diphenylmethyl)azetidin-3-yl)-1,2-dimethylpiperazine → (R)-4-(Azetidin-3-YL)-1,2-dimethylpiperazine

HRID 707518Notes

Reaction equation

HRID 707518 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[C@H:14]([CH3:19])[CH2:13]3)[CH2:9]2)C=CC=CC=1>[OH-].[Pd+2].[OH-].[C].CO>[NH:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C@H:14]([CH3:19])[CH2:13]2)[CH2:9]1

Participants

4

Reactant 1

HCID 118162432(2R)-4-(1-(Diphenylmethyl)azetidin-3-yl)-1,2-dimethylpiperazine

Product 1

HCID 118162417(R)-4-(Azetidin-3-YL)-1,2-dimethylpiperazineYield 166.2%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

To a mixed solution of (2R)-4-(1-(diphenylmethyl)azetidin-3-yl)-1,2-dimethylpiperazine (342 mg, 1.02 mmol) described in Production Example 5-2 and methanol (10 mL) was added palladium hydroxide-carbon (200 mg) at room temperature. The resultant mixture was stirred under a hydrogen atmosphere at room temperature and at 0.35 MPa to 0.40 MPa for 5 hours. The reaction mixture was purged with a nitrogen atmosphere, and then filtrated using Celite. A filtrate was concentrated under a reduced pressure to give a mixture (287 mg) of the title compound and benzylbenzene. The product was used in the subsequent reaction without further purification.

Workup

  1. customThe reaction mixture was purged with a nitrogen atmosphere
  2. filtrationfiltrated
  3. concentrationA filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-22568a4e58624ec8883ce825e30d5d99
Source dataset
uspto-grants-2015_11
Patent number
US09174998B2

Reaction notes

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