Water → 3-Amino-1-(diphenylmethyl)azetidine

HRID 1766190Notes

Reaction equation

HRID 1766190 reaction equation
CN.O.[C:4]1([CH:10]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:11]2[CH2:14][CH:13]([N:15]3C(=O)C4=CC=CC=C4C3=O)[CH2:12]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[NH2:15][CH:13]1[CH2:14][N:11]([CH:10]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 6329Methylamine2×HCID 134919172-[1-(diphenylmethyl)azetidin-3-yl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 57445463-Amino-1-(diphenylmethyl)azetidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

572 ml of 40% aqueous methylamine solution and 300 ml of water were added successively to a suspension of 78.0 g (0.212 mol) of 1-(diphenylmethyl)-3-(phthalimido)-azetidine in 480 ml of ethanol. After 7 days' stirring at ambient temperature a clear solution had formed, which was freed from excess methylamine and ethanol in vacuo. The aqueous solution remaining was extracted exhaustively with ethyl acetate. The ethyl acetate extracts were dried over sodium sulphate and dried in vacuo. 45.0 g (89% of theoretical) of a colourless oil were obtained, which was further processed without any additional purification.

Workup

  1. customhad formed
  2. extractionThe aqueous solution remaining was extracted exhaustively with ethyl acetate
  3. dry with materialThe ethyl acetate extracts were dried over sodium sulphate
  4. customdried in vacuo
  5. custom45.0 g (89% of theoretical) of a colourless oil were obtained
  6. customwhich was further processed without any additional purification

Sources & evidence

ORD record
ord-dc22f787f90f44e4818d1e3b99bf49fb
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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