Water → 1-(Diphenylmethyl)azetidine-3-carbonitrile

HRID 1712645Notes

Reaction equation

HRID 1712645 reaction equation
O.[O-][C:3]#[N:4].[Na+].[CH:6]([N:19]1[CH2:22][CH:21](OS(C)(=O)=O)[CH2:20]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH:6]([N:19]1[CH2:22][CH:21]([C:3]#[N:4])[CH2:20]1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 517096Sodium CyanateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 27792901-(Diphenylmethyl)azetidine-3-carbonitrileYield 92.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

Water (7.2 ml) and sodium cyanate (3.48 g) were added to a solution of 1-benzhydryl-3-(methanesulfonyloxy)azetidine (7.52 g) in N,N-dimethylformamide (60 ml), followed by stirring at 65° C. for 9 hours. Water, sodium carbonate and ethyl acetate were added to the reaction mixture, which was partitioned. The aqueous layer was extracted with ethyl acetate. The organic layer was collected, washed with brine, and dried over anhydrous sodium sulfate. This was concentrated under reduced pressure, and the resultant crystals were suspended by addition of diethyl ether (10 ml). The crystals were collected by filtration, and washed with diethyl ether. This was dried under aeration to give the title compound (5.43 g, 92.3%) as pale yellow crystals.

Workup

  1. customwas partitioned
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. customThe organic layer was collected
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThis was concentrated under reduced pressure
  7. additionthe resultant crystals were suspended by addition of diethyl ether (10 ml)
  8. filtrationThe crystals were collected by filtration
  9. washwashed with diethyl ether
  10. customThis was dried under aeration

Sources & evidence

ORD record
ord-ad9a7ef4b7a544ff9a39404133548214
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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