Hydrochloric Acid → HCID 20254312, compound

HRID 638343Notes

Reaction equation

HRID 638343 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[CH:12]3[CH2:13][CH2:14][CH2:15][CH:8]2[CH2:9][C:10](=[N:16]O)[CH2:11]3)=[CH:4][CH:3]=1.[Na].Cl>C(O)CCCC.CCOCC>[NH2:16][CH:10]1[CH2:9][CH:8]2[N:7]([CH2:6][C:5]3[CH:18]=[CH:19][C:2]([CH3:1])=[CH:3][CH:4]=3)[CH:12]([CH2:13][CH2:14][CH2:15]2)[CH2:11]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545Sodium2×HCID 20254313HCID 20254313, compound

Product 1

HCID 20254312HCID 20254312, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 62761-PentanolSolvent

Procedure

9-(4-Methylbenzyl)-9-aza-bicyclo-[3.3.1]-nonan-3-one oxime (4 g) was dissolved in amyl alcohol (100 ml) and heated to reflux. Sodium (2 g) was added portionwise whilst the solution was stirred. After all the sodium had dissolved, the solution was cooled, diluted with ether and acidified with dilute hydrochloric acid. The acid extract was washed with ether and then basified with excess potassium carbonate. Extraction with ethyl acetate followed by evaporation of solvent afforded crude 3-amino-9-(4-methylbenzyl)-9-azabicyclo[3.3.1]-nonane (3.6 g, 95%) used in the next procedure without purification.

Workup

  1. temperatureheated to reflux
  2. temperaturethe solution was cooled
  3. extractionThe acid extract
  4. washwas washed with ether
  5. extractionExtraction with ethyl acetate
  6. customfollowed by evaporation of solvent

Sources & evidence

ORD record
ord-cbeacad64d9841d2b01f657977290aca
Source dataset
uspto-grants-1985_12
Patent number
US04560757

Reaction notes

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