Benzoyl chloride → N-(9-cyanobicyclo[3.3.1]non-9-yl)benzamide

HRID 1040336Notes

Reaction equation

HRID 1040336 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:16][C:17]1([C:26]#[N:27])[CH:22]2[CH2:23][CH2:24][CH2:25][CH:18]1[CH2:19][CH2:20][CH2:21]2.C(Cl)Cl.O>O.C1COCC1>[C:26]([C:17]1([NH:16][C:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:18]2[CH2:19][CH2:20][CH2:21][CH:22]1[CH2:23][CH2:24][CH2:25]2)#[N:27]

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 21908982Water methylene chlorideHCID 667208249-Aminobicyclo[3.3.1]nonane-9-carbonitrile

Product 1

HCID 66721238N-(9-cyanobicyclo[3.3.1]non-9-yl)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add a solution of 2.37 g (17.17 mmol) of potassium carbonate in 30 mL of water, then 1.37 mL (11.8 mmol) of benzoyl chloride, to a solution of 1.88 g (11.45 mmol) of 9-aminobicyclo[3.3.1]nonane-9-carbonitrile in 20 mL of THF. Stir the reaction mixture for 1 h at RT, then distribute in 100 mL of a 1:1 mixture of DCM/water. Wash the organic phase with 50 mL of water, dry over Na2SO4 and concentrate under reduced pressure. Solidify the residue obtained in 100 mL of pentane giving, after filtration and washing with pentane, 2.81 g of N-(9-cyanobicyclo[3.3.1]non-9-yl)benzamide in the form of white powder.

Workup

  1. washWash the organic phase with 50 mL of water
  2. dry with materialdry over Na2SO4
  3. concentrationconcentrate under reduced pressure
  4. customobtained in 100 mL of pentane giving
  5. filtrationafter filtration
  6. washwashing with pentane, 2.81 g of N-(9-cyanobicyclo[3.3.1]non-9-yl)benzamide in the form of white powder

Sources & evidence

ORD record
ord-04462028245c4e4398c495e5996603eb
Source dataset
uspto-grants-2013_10
Patent number
US08552201B2

Reaction notes

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