Ammonia → 3-Amino-1-benzhydryl-3-propylazetidine

HRID 743648Notes

Reaction equation

HRID 743648 reaction equation
[CH:1]([N:14]1[CH2:17][C:16](OS(C)(=O)=O)([CH2:18][CH2:19][CH3:20])[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.[NH3:26]>C(O)C>[NH2:26][C:16]1([CH2:18][CH2:19][CH3:20])[CH2:17][N:14]([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:15]1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 194236241-Benzhydryl-3-methanesulphonyloxy-3-propylazetidine

Product 1

HCID 194237003-Amino-1-benzhydryl-3-propylazetidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

7.5 g of 1-benzhydryl-3-methanesulphonyloxy-3-propyl-azetidine are added to a solution at approximately 5° C. of 100 cm3 of a solution of ammonia in ethanol (prepared from 15 g of ammonia in 100 cm3 of ethanol at 5° C., the temperature is allowed to rise to approximately 20° C. and the mixture is stirred for 16 hours at the same temperature. After concentration to dryness under reduced pressure (20 kPa) at approximately 40° C., the residue is taken up with 25 cm3 of water and 2.22 g of methanesulphonic acid. The aqueous phase is washed with twice 25 cm3 of ethyl ether, treated with 10 cm3 of 40% aqueous sodium hydroxide and extracted with 3 times 50 cm3 of dichloromethane; the combined organic extracts are washed with 10 cm3 of water saturated with sodium chloride, dried over magnesium sulphate and concentrated to dryness under the above conditions. 5.2 g of 3-amino-1-benzhydryl-3-propylazetidine are obtained in the form of an oily product, which is used without further purification for the subsequent steps.

Workup

  1. customto rise to approximately 20° C.
  2. concentrationAfter concentration to dryness under reduced pressure (20 kPa) at approximately 40° C.
  3. washThe aqueous phase is washed with twice 25 cm3 of ethyl ether
  4. additiontreated with 10 cm3 of 40% aqueous sodium hydroxide
  5. extractionextracted with 3 times 50 cm3 of dichloromethane
  6. washthe combined organic extracts are washed with 10 cm3 of water saturated with sodium chloride
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated to dryness under the above conditions

Sources & evidence

ORD record
ord-4b3694707b0f4bd7a3ecd8b0c877ee8b
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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