1-(1-Benzhydrylazetidin-3-yl)-4-methylpiperazine → 1-(Azetidin-3-yl)-4-methylpiperazine

HRID 707510Notes

Reaction equation

HRID 707510 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][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])[CH2:14][CH2:13]2)[CH2:9]1

Participants

4

Reactant 1

HCID 222591561-(1-Benzhydrylazetidin-3-yl)-4-methylpiperazine

Product 1

HCID 206598001-(Azetidin-3-yl)-4-methylpiperazine

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

To a mixed solution of 1-(1-(diphenylmethyl)azetidin-3-yl)-4-methylpiperazine (1.21 g, 3.75 mmol) described in Production Example 3-1 and methanol (20 mL) was added palladium hydroxide-carbon (500 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 4 hours and 45 minutes. The reaction mixture was purged with a nitrogen atmosphere, and then filtrated using Celite. A filtrate was concentrated under a reduced pressure to give the title compound in the form of a mixture (1.00 g) with 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-04d896f6073f468eb4c0eebe9daa384d
Source dataset
uspto-grants-2015_11
Patent number
US09174998B2

Reaction notes

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