Dimethylamine → 1-Benzhydryl-N,N-dimethylazetidin-3-amine

HRID 1437234Notes

Reaction equation

HRID 1437234 reaction equation
[CH:1]([N:14]1[CH2:17][C:16](=O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][NH:20][CH3:21].[H][H]>CO.[C].[Pd]>[CH:1]([N:14]1[CH2:17][CH:16]([N:20]([CH3:21])[CH3:19])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 104681521-Benzhydryl-N,N-dimethylazetidin-3-amineYield 92%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

5% Palladium-carbon (1.5 g) was added to 1-benzhydrylazetidin-3-one (1.50 g) obtained from Referential Example 100 and 40% aqueous dimethylamine (4 mL) in methanol (30 mL). The resultant mixture was subjected to catalytic reduction in a hydrogen atmosphere overnight. The catalyst was filtered off, and then the solvent of the filtrate was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give the title compound as a solid (1.55 g, 92%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent of the filtrate was evaporated under reduced pressure
  3. customThe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-ab8c268c2e294485ab275cb4c71d4bc1
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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