Benzylamine → 3-(Benzylamino)oxetan-3-acetonitrile

HRID 539991Notes

Reaction equation

HRID 539991 reaction equation
[O:1]1[CH2:4][C:3](=[CH:5][C:6]#[N:7])[CH2:2]1.[C:8]1([CH2:14][NH2:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[CH2:14]([NH:15][C:3]1([CH2:5][C:6]#[N:7])[CH2:4][O:1][CH2:2]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 533465742-(3-Oxetanylidene)acetonitrile

Product 1

HCID 712544323-(Benzylamino)oxetan-3-acetonitrileYield 81.7%

Conditions

Temperature
60 °C

Procedure

A mixture of oxetan-3-ylidene-acetonitrile (950 mg, 10 mmol) and phenylmethanamine (1.31 ml, 12 mmol) was heated with stirring at 60° C. for 5 hours under nitrogen. The mixture was concentrated in vacuo. The residue was purified by flash column (eluting with 0-50% ethyl acetate in hexane) to afford 1.65 g of 3-(benzylamino)oxetan-3-acetonitrile as a colorless oil (yield was 81.7%).

Workup

  1. temperaturewas heated
  2. concentrationThe mixture was concentrated in vacuo
  3. customThe residue was purified by flash column (eluting with 0-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f6fb773555f448fcb701bb36f3d522de
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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