(2S)-1-(1-(Diphenylmethyl)azetidin-3-yl)-2,4-dimethylpiperazine → (2S)-1-(azetidin-3-yl)-2,4-dimethylpiperazine

HRID 707522Notes

Reaction equation

HRID 707522 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])[CH2:14][C@@H:13]3[CH3:19])[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])[CH2:14][C@@H:13]2[CH3:19])[CH2:9]1

Participants

4

Reactant 1

HCID 118162470(2S)-1-(1-(Diphenylmethyl)azetidin-3-yl)-2,4-dimethylpiperazine

Product 1

HCID 118162468(2S)-1-(azetidin-3-yl)-2,4-dimethylpiperazineYield 162.4%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

To a mixed solution of (2S)-1-(1-(diphenylmethyl)azetidin-3-yl)-2,4-dimethylpiperazine (321 mg, 0.957 mmol) described in Production Example 6-2 and methanol (7.0 mL) was added palladium hydroxide-carbon (150 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 (263 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-71649c2afee24cc489d6810e341511be
Source dataset
uspto-grants-2015_11
Patent number
US09174998B2

Reaction notes

Loading…