Acetic Acid → 1-azetidin-3-yl-N,N-dimethylpiperidine-4-carboxamide

HRID 426089Notes

Reaction equation

HRID 426089 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]([N:20]([CH3:22])[CH3:21])=[O:19])[CH2:14][CH2:13]3)[CH2:9]2)C=CC=CC=1.C(O)(=O)C>CO.[OH-].[OH-].[Pd+2]>[NH:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]([N:20]([CH3:22])[CH3:21])=[O:19])[CH2:14][CH2:13]2)[CH2:9]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 236589531-[1-(diphenylmethyl)azetidin-3-yl]-N,N-dimethylpiperidine-4-carboxamide

Product 1

HCID 236587821-azetidin-3-yl-N,N-dimethylpiperidine-4-carboxamideYield 98.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Palladium hydroxide on carbon (0.10 g) was placed in a 5 mL vial intended for microwave synthesis. 1-[1-(Diphenylmethyl)azetidin-3-yl]-N,N-dimethylpiperidine-4-carboxamide (0.20 g, 0.53 mmol) dissolved in methanol (3 mL) and acetic acid (0.3 mL) was added. The mixture was stirred under hydrogen (1.6 bar) at RT for four days. The mixture was filtered through a plug of Celite®. The solvent was removed by evaporation and there was obtained 0.11 g (53%) of the title compound.

Workup

  1. customvial intended for microwave synthesis
  2. filtrationThe mixture was filtered through a plug of Celite®
  3. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-ef31420606c14d549d60556f318a9465
Source dataset
uspto-grants-2012_01
Patent number
US08106208B2

Reaction notes

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