Pyridine → HCID 54509534, compound

HRID 2398646Notes

Reaction equation

HRID 2398646 reaction equation
[CH:1]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:3]([N:4]([CH2:12][CH2:13][C:14]([C:27]4[NH:31][N:30]=NN=4)([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:5]3)[CH2:2]1)[CH2:9]2.[C:32](OC(=O)C)(=[O:34])[CH3:33].N1C=CC=CC=1>O>[CH:8]12[CH2:7][CH:6]3[CH2:11][CH:1]([CH2:2][CH:3]([N:4]([CH2:12][CH2:13][C:14]([C:27]4[O:34][C:32]([CH3:33])=[N:30][N:31]=4)([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:5]3)[CH2:10]1)[CH2:9]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 178420259HCID 178420259, compound

Product 1

HCID 54509534HCID 54509534, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 48 parts of 5-{3-[4-azatricyclo(4.3.1.13,8)undecan-4-yl]-1,1-diphenylpropyl}-1H-tetrazole and 140 parts of acetic anhydride in 400 parts of pyridine is heated at the boiling point under reflux for 3 hours, then cooled and thereupon diluted with 100 parts of water. The resultant mixture is stirred for 10 minutes, whereupon solvent is removed by vacuum distillation and the residue partitioned between a saturated aqueous solution of sodium bicarbonate and diethyl ether. The ethereal phase is separated and consecutively washed with a saturated aqueous solution of sodium bicarbonate and water, then extracted with 2% hydrochloric acid. The acid extract is made alkaline, and the resultant mixture is extracted with ether. The ether extract is washed with water, dried over anhydrous sodium sulfate, and filtered. The filtrate, stripped of solvent by vacuum distillation, affords 2-{3-[4-azatricyclo(4.3.1.13,8)undecan-4-yl]-1,1-diphenylpropyl}-5-methyl-1,3,4-oxadiazole melting at approximately 120°-121° as the residue. It has the formula ##STR11##

Workup

  1. temperatureunder reflux for 3 hours
  2. temperaturecooled
  3. customis removed by vacuum distillation
  4. customthe residue partitioned between a saturated aqueous solution of sodium bicarbonate and diethyl ether
  5. customThe ethereal phase is separated
  6. washconsecutively washed with a saturated aqueous solution of sodium bicarbonate and water
  7. extractionextracted with 2% hydrochloric acid
  8. extractionThe acid extract
  9. extractionthe resultant mixture is extracted with ether
  10. extractionThe ether extract
  11. washis washed with water
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. distillationThe filtrate, stripped of solvent by vacuum distillation

Sources & evidence

ORD record
ord-0d07232f746a4672a0748737d7e70312
Source dataset
uspto-grants-1977_05
Patent number
US04025524

Reaction notes

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