Cyclopropylamine → 1-Benzhydryl-3-cyclopropylamino-3-methylazetidine

HRID 743662Notes

Reaction equation

HRID 743662 reaction equation
[CH:1]([N:14]1[CH2:17][C:16](OS(C)(=O)=O)([CH3:18])[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.[CH:24]1([NH2:27])[CH2:26][CH2:25]1>C(O)C>[CH:1]([N:14]1[CH2:17][C:16]([NH:27][CH:24]2[CH2:26][CH2:25]2)([CH3:18])[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

4

Reactant 2

HCID 69828CyclopropylamineHCID 100652951-Benzhydryl-3-methylazetidin-3-yl methanesulfonate

Product 1

HCID 194237611-Benzhydryl-3-cyclopropylamino-3-methylazetidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 16.6 g of 1-benzhydryl-3-methane-sulphonyloxy-3-methylazetidine and 28.84 g of of cyclopropylamine in 250 cm3 of ethanol is stirred for 96 hours at approximately 20° C. The reaction mixture is concentrated under reduced pressure (20 kPa) at approximately 30° C. The dry extract is taken up with 50 cm3 of water and 8.8 g of methanesulphonic acid. The aqueous phase is washed with 3 times 25 cm3 of dichloromethane, treated with 12 cm3 of 35% aqueous sodium hydroxide and extracted with 3 times 50 cm3 of ethyl acetate. The combined organic phases are washed with twice 50 cm3 of water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (20 kPa) at approximately 25° C. 14.6 g of 1-benzhydryl-3-cyclopropylamino-3-methylazetidine are obtained in the form of a yellow oil, which is used without further purification for the subsequent steps.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure (20 kPa) at approximately 30° C
  2. extractionThe dry extract
  3. washThe aqueous phase is washed with 3 times 25 cm3 of dichloromethane
  4. additiontreated with 12 cm3 of 35% aqueous sodium hydroxide
  5. extractionextracted with 3 times 50 cm3 of ethyl acetate
  6. washThe combined organic phases are washed with twice 50 cm3 of water
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated to dryness under reduced pressure (20 kPa) at approximately 25° C

Sources & evidence

ORD record
ord-81ebc4220b2243008e8407ff058364ab
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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