3-Pyridinecarbonyl chloride, hydrochloride (1:1) → HCID 68146112, compound

HRID 1580153Notes

Reaction equation

HRID 1580153 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]23[CH2:17][CH:12]([N:13]([CH3:16])[CH:14]2[CH3:15])[CH2:11][CH2:10][CH2:9]3)[CH:5]=[CH:6][CH:7]=1.[ClH:18].[C:19]([Cl:27])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=1>N1C=CC=CC=1>[OH2:1].[ClH:27].[ClH:18].[C:19]([O:1][C:2]1[CH:3]=[C:4]([C:8]23[CH2:17][CH:12]([N:13]([CH3:16])[CH:14]2[CH3:15])[CH2:11][CH2:10][CH2:9]3)[CH:5]=[CH:6][CH:7]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=1.[C:19]([O:1][C:2]1[CH:3]=[C:4]([C:8]23[CH2:17][CH:12]([N:13]([CH3:16])[CH:14]2[CH3:15])[CH2:11][CH2:10][CH2:9]3)[CH:5]=[CH:6][CH:7]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=1.[ClH:27].[ClH:27]

Participants

4

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 3045735HCID 3045735, compound

Product 1

HCID 68146112HCID 68146112, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 0.231 g of 1-(3-hydroxyphenyl)-6,7-dimethyl-6-azabicyclo[3,2,1]octane in 4 ml of pyridine is added 0.376 g of nicotinoyl chloride hydrochloride under icecooling. The solution is stirred at room temperature overnight. Then, the solution is concentrated under reduced pressure. The resudue thus obtained is washed with ether, and then recrystallized from a mixture of ethanol, acetone and ether. 0.17 g of 1-(3-nicotinoyloxyphenyl)-6,7-dimethyl-6-azabicyclo[3,2,1]octane dihydrochloride hemihydrate is obtained. M.p. 210° - 218°C.

Workup

  1. concentrationThen, the solution is concentrated under reduced pressure
  2. customThe resudue thus obtained
  3. washis washed with ether
  4. customrecrystallized from a mixture of ethanol, acetone and ether

Sources & evidence

ORD record
ord-33493eadcd9649e38cbf431cd84d2307
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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