Benzoyl chloride → HCID 14367993, compound

HRID 544588Notes

Reaction equation

HRID 544588 reaction equation
[CH3:1][N:2]1[CH2:9][CH:8]2[CH:10]([OH:11])[CH:4]([CH2:5][N:6]([CH3:12])[CH2:7]2)[CH2:3]1.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:12][N:6]1[CH2:5][CH:4]2[CH:10]([O:11][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]([CH2:9][N:2]([CH3:1])[CH2:3]2)[CH2:7]1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 123608323,7-Dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-ol

Product 1

HCID 14367993HCID 14367993, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

10 g of 3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonane-9-ol are dissolved in 50 ml of dry pyridine, and a solution of 11.24 g of benzoyl chloride in 50 ml of dry pyridine is added dropwise, within 30 minutes, to the solution stirred at 5°-10° C. Thereafter the reaction mixture is stirred at room temperature for 3 hours, and the bulk of pyridine is distilled off under vacuo. The residue is taken up in 50 ml of water, the mixture is acidified with 20 ml of concentrated aqueous hydrochloric acid, and the mixture is extracted thrice with 50 ml of ether, each, in order to remove the non-basic substances. The aqueous phase is rendered alkaline with potassium carbonate and extracted thrice with 50 ml of chloroform, each. The chloroform solutions are combined, dried over magnesium sulfate, filtered, and the filtrate is evaporated. The residue is crystallized from n-hexane. 3,7-Dimethyl-9-benzoyloxy-3,7-diazabicyclo[3.3.1]nonane is obtained with a yield of 42.5%; m.p.: 100°-102° C.

Workup

  1. stirringThereafter the reaction mixture is stirred at room temperature for 3 hours
  2. distillationthe bulk of pyridine is distilled off under vacuo
  3. extractionthe mixture is extracted thrice with 50 ml of ether
  4. customeach, in order to remove the non-basic substances
  5. extractionextracted thrice with 50 ml of chloroform
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated
  9. customThe residue is crystallized from n-hexane

Sources & evidence

ORD record
ord-530fece2ec3e4ebabbef8075edfa884c
Source dataset
uspto-grants-1984_05
Patent number
US04451473

Reaction notes

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