Benzhydrylamine → 1-Benzhydrylazetidine-2-carbonitrile

HRID 1390958Notes

Reaction equation

HRID 1390958 reaction equation
Br[CH:2]([CH2:5][CH2:6]Br)[C:3]#[N:4].[CH:8]([NH2:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[CH:8]([N:21]1[CH2:6][CH2:5][CH:2]1[C:3]#[N:4])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 516892Sodium BicarbonateHCID 153091472,4-Dibromobutanenitrile

Product 1

HCID 197720721-Benzhydrylazetidine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Reflux for 18 hours, a stirred mixture of 10 g of 2,4-dibromobutyronitrile, 7.35 g of benzhydrylamine, and 7.41 g of sodium bicarbonate in 100 ml of acetonitrile. Filter off the solids and remove the acetonitrile in vacuo. Treat the residue with ether and filter out insoluble solids. Wash the ether solution first with water, then with a solution of 5.40 g of oxalic acid in 200 ml of water, and finally with brine (saturated aqueous NaCl solution). Dry the solution over anhydrous magnesium sulfate and remove solvent in vacuo. Crystallize the solid residue from methylene chloride-hexane to obtain the analytically pure title compound, m.p. 103.5°-105.0° C.

Workup

  1. temperatureReflux for 18 hours
  2. filtrationFilter off the solids
  3. customremove the acetonitrile in vacuo
  4. additionTreat the residue with ether
  5. filtrationfilter out insoluble solids
  6. washWash the ether solution first with water
  7. dry with materialDry the solution over anhydrous magnesium sulfate
  8. customremove solvent in vacuo
  9. customCrystallize the solid residue from methylene chloride-hexane

Sources & evidence

ORD record
ord-42ebcc55d1d049de9125da131b79904d
Source dataset
uspto-grants-1979_02
Patent number
US04140780

Reaction notes

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