Acetic Acid → 1-(Diphenylmethyl)-3-(methylamino)-3-azetidinecarbonitrile

HRID 1246804Notes

Reaction equation

HRID 1246804 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.Cl.[CH3:20][NH2:21].C(O)(=O)C.[C-:26]#[N:27].[K+]>CO>[CH:1]([N:14]1[CH2:17][C:16]([NH:27][CH3:26])([C:20]#[N:21])[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 9032Potassium CyanideHCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 6364545Methylamine hydrochloride

Product 1

HCID 219057751-(Diphenylmethyl)-3-(methylamino)-3-azetidinecarbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-benzhydrylazetidin-3-one (2.13 g, 8.98 mmol) in methanol (17 ml) was added methylamine hydrochloride (1.21 g, 18.0 mmol) and then acetic acid (1.03 ml, 18.0 mmol) at room temperature. After stirring for 5 minutes, solid KCN (1.17 g, 18.0 mmol) was added and the mixture was heated to 60° C. for 19 hours. The reaction was cooled; the solid product was collected by vacuum filtration, rinsed with methanol, and then dried, in vacuo, to afford I-(29A-7)a as a colorless solid (2.50 g, quantitative): +ES MS (M+1) 278.3; 1H NMR (400 MHz, CD2Cl2) δ 7.43 (d, J=7.5 Hz, 4H), 7.29 (t, J=7.5 Hz, 4H), 7.23 (t, J=7.3 Hz, 2H), 4.45 (s, 1H), 3.55 (d, J=7.5 Hz, 2H), 3.15 (d, J=7.1 Hz, 2H), 2.40 (s, 3H).

Workup

  1. customat room temperature
  2. temperatureThe reaction was cooled
  3. filtrationthe solid product was collected by vacuum filtration
  4. washrinsed with methanol
  5. customdried, in vacuo
  6. customto afford I-(29A-7)a as a colorless solid (2.50 g, quantitative)

Sources & evidence

ORD record
ord-14e3682b51c9486fbe7074152353caca
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

Loading…