3-Chlorobenzoic Acid → 3-Chloro-N-(3-quinuclidinyl)benzamide

HRID 1742817Notes

Reaction equation

HRID 1742817 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.C1(N=C=NC2CCCCC2)CCCCC1.O.ON1C2C=CC=CC=2N=N1.[NH2:37][CH:38]1[CH:43]2[CH2:44][CH2:45][N:40]([CH2:41][CH2:42]2)[CH2:39]1>C(#N)C>[N:40]12[CH2:45][CH2:44][CH:43]([CH2:42][CH2:41]1)[CH:38]([NH:37][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=1)[CH2:39]2

Participants

6

Reactant 4

HCID 4473-Chlorobenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 1232383-AminoquinuclidineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 28025403-Chloro-N-(3-quinuclidinyl)benzamideYield 99.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 400 ml of acetonitrile was suspended 25 g of m-chlorobenzoic acid and while the suspension was stirred with ice-cooling, 39.5 g of N,N'-dicyclohexylcarbodiimide and 27.0 g of 1-hydroxybenzotriazole monohydrate were added. The mixture was stirred for 2 hours. Then, 20.2 g of 3-aminoquinuclidine was added and the mixture was further stirred with ice-cooling for 2 hours and, then, at room temperature for 20 hours. The reaction mixture was filtered to remove insolubles and the solvent was evaporated off. The residue was dissolved by addition of diluted hydrochloric acid and washed twice with ethyl acetate. The aqueous layer was neutralized with aqueous solution of sodium hydroxide and extracted with chloroform. The extract was washed with water and dried over anhydrous magnesium sulfate and the chloroform was evaporated off to give 42.1 g of the desired compound as white crystals.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 2 hours
  3. stirringthe mixture was further stirred with ice-
  4. temperaturecooling for 2 hours
  5. filtrationThe reaction mixture was filtered
  6. customto remove insolubles
  7. customthe solvent was evaporated off
  8. dissolutionThe residue was dissolved by addition of diluted hydrochloric acid
  9. washwashed twice with ethyl acetate
  10. extractionextracted with chloroform
  11. washThe extract was washed with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customthe chloroform was evaporated off

Sources & evidence

ORD record
ord-105da8c89b88464a9d2c4c046de3eee8
Source dataset
uspto-grants-1994_08
Patent number
US05342845

Reaction notes

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