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

HRID 1842694Notes

Reaction equation

HRID 1842694 reaction equation
[CH3:1][NH:2][CH3:3].[CH:4]([N:17]1[CH2:20][CH:19](CS([O-])(=O)=O)[CH2:18]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CC#N>[CH:4]([N:17]1[CH2:20][CH:19]([N:2]([CH3:3])[CH3:1])[CH2:18]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 71431707(1-Benzhydrylazetidin-3-yl)methanesulfonate2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Aqueous dimethylamine (1 L, 33%) was added to a solution of (1-benzhydrylazetidin-3-yl)methanesulfonate (Intermediate 30, 260 g, 0.82 mol) in CH3CN (1 L) and the mixture was refluxed at 100° C. overnight. The mixture was then cooled and the solvent was removed in vacuo. The mixture was partitioned between water (300 mL) and CH2Cl2 (300 mL) and the layers were separated. The aqueous phase was extracted with CH2Cl2 (3×500 mL). The combined organic solutions were dried (Na2SO4) and concentrated in vacuo. Purification by FCC gave the title compound (200 g, 92%) as a brown solid.

Workup

  1. temperatureThe mixture was then cooled
  2. customthe solvent was removed in vacuo
  3. customThe mixture was partitioned between water (300 mL) and CH2Cl2 (300 mL)
  4. customthe layers were separated
  5. extractionThe aqueous phase was extracted with CH2Cl2 (3×500 mL)
  6. dry with materialThe combined organic solutions were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customPurification by FCC

Sources & evidence

ORD record
ord-1c77098ced2e4e19bdea4ca5dabf3d4e
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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