Acetic Acid → 1-Benzhydryl-3-benzylaminoazetidine-3-carbonitrile

HRID 2054391Notes

Reaction equation

HRID 2054391 reaction equation
[CH:1]([N:14]1[CH2:17][C:16](=O)[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.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O)(=O)C.[C-:31]#[N:32].[Na+]>CO>[CH:1]([N:14]1[CH2:17][C:16]([NH:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:31]#[N:32])[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

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 8929Sodium CyanideHCID 37355581-(Diphenylmethyl)azetidin-3-one

Product 1

HCID 219057811-Benzhydryl-3-benzylaminoazetidine-3-carbonitrileYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-benzhydrylazetidin-3-one (3.3 g, 14 mmol) in methanol (35 ml) was added benzylamine (1.6 ml, 15 mmol) and then acetic acid (0.88 ml, 15 mmol) at room temperature. After stirring for 45 minutes, solid NaCN (0.76 g, 15 mmol) was added in portions over 2 minutes and the mixture was heated to reflux overnight. The reaction, which now contained a precipitate, was cooled and then stirred at room temperature. The solids were collected by vacuum filtration, rinsed with a small volume of cold methanol, and then dried, in vacuo, to give I-2A-1c as a solid (3.56 g, 72%): +APcI MS (M+1) 354.4; 1H NMR (400 MHz, CD3OD) δ 7.40 (d, J=7.5 Hz, 4H), 7.35 (d, J=7.5 Hz, 2H), 7.31-7.20 (m, 7H), 7.16 (t, J=7.3 Hz, 2H), 4.44 (s, 1H), 3.76 (s, 2H), 3.48 (d, J=8.3 Hz, 2H), 3.05 (d, J=8.3 Hz, 2H).

Workup

  1. customat room temperature
  2. temperaturethe mixture was heated
  3. temperatureto reflux overnight
  4. customThe reaction, which
  5. temperaturewas cooled
  6. stirringstirred at room temperature
  7. filtrationThe solids were collected by vacuum filtration
  8. washrinsed with a small volume of cold methanol
  9. customdried, in vacuo

Sources & evidence

ORD record
ord-8727577979564c5cb7f8ec88f64b6ee3
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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