2-Chloro-N-pyridin-2-yl-acetamide → (R)-3-(1-Phenyl-cycloheptanecarbonyloxy)-1-(pyridin-2-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane chloride

HRID 2192334Notes

Reaction equation

HRID 2192334 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[Cl:25][CH2:26][C:27]([NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)=[O:28]>C(#N)C>[Cl-:25].[C:19]1([C:12]2([C:10]([O:9][C@@H:3]3[CH:4]4[CH2:7][CH2:8][N+:1]([CH2:26][C:27](=[O:28])[NH:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=5)([CH2:6][CH2:5]4)[CH2:2]3)=[O:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 2894352-Chloro-N-pyridin-2-yl-acetamideHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 53311101(R)-3-(1-Phenyl-cycloheptanecarbonyloxy)-1-(pyridin-2-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane chlorideYield 55.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester (Example 14e) (254 mg, 0.78 mmol) in acetonitrile (5 mL) was treated with 2-chloro-N-pyridin-2-yl-acetamide (Example 14f) (146 mg) and the resulting yellow solution was stirred at room temperature overnight during which a solid precipitated. The reaction mixture was treated with a couple of mLs of ether and the solid was filtered off, washed with ether and dried under vacuum to give the title compound (217 mg) as an off-white solid. Crystallisation from refluxing acetonitrile (20 mL) gave 98 mg of the title compound as a white crystalline solid.

Workup

  1. customprecipitated
  2. additionThe reaction mixture was treated with a couple of mLs of ether
  3. filtrationthe solid was filtered off
  4. washwashed with ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-a382a266ee9c49bb854d8deb518adefb
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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