Dibenzylamine → 3-(Dibenzylamino)oxetane-3-carbonitrile

HRID 2275840Notes

Reaction equation

HRID 2275840 reaction equation
[O:1]1[CH2:4][C:3](=O)[CH2:2]1.C[Si]([C:10]#[N:11])(C)C.[CH2:12]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)(=O)C>[CH2:20]([N:19]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]1([C:10]#[N:11])[CH2:4][O:1][CH2:2]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7656DibenzylamineHCID 82115Trimethylsilyl cyanideHCID 150242543-Oxetanone

Product 1

HCID 574159013-(Dibenzylamino)oxetane-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.63 ml (10.8 mmol) of oxetan-3-one and 3.6 ml (27.1 mmol) of trimethylsilyl cyanide were added to 10.4 ml (54.1 mmol) of dibenzylamine in 72 ml of acetic acid. The reaction mixture was then stirred at RT overnight. The mixture was then concentrated, the residue was dissolved in water/diethyl ether and the aqueous phase was extracted twice with diethyl ether. The combined organic phases were washed twice with saturated aqueous sodium bicarbonate solution, dried over sodium sulphate, filtered and concentrated. The residue was purified by silica gel chromatography (cyclohexane/ethyl acetate from 40:1 to 30:1). This gave 2.39 g (77% of theory, purity 97%) of the target compound.

Workup

  1. concentrationThe mixture was then concentrated
  2. dissolutionthe residue was dissolved in water/diethyl ether
  3. extractionthe aqueous phase was extracted twice with diethyl ether
  4. washThe combined organic phases were washed twice with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (cyclohexane/ethyl acetate from 40:1 to 30:1)

Sources & evidence

ORD record
ord-b0cf3f3610de4b38805cf11958d5fc93
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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