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

HRID 1246795Notes

Reaction equation

HRID 1246795 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 solid were collected by vacuum filtration, rinsed with a small volume of cold methanol, and then dried, in vacuo, to give I-(13A-9)a as a solid (3.56 g, 72%): +ACPI 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 solid were collected by vacuum filtration
  8. washrinsed with a small volume of cold methanol
  9. customdried, in vacuo

Sources & evidence

ORD record
ord-a8dece8dd24b48f68cefb32b7394f4ab
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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