Water → HCID 21278098, compound

HRID 2291814Notes

Reaction equation

HRID 2291814 reaction equation
[Na].[ClH:2].[N:3]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[C:6](=[N:12]O)[CH2:5][CH2:4]2.O>C(O)CCCC>[ClH:2].[NH2:12][CH:6]1[CH:7]2[CH2:10][CH2:11][N:3]([CH2:9][CH2:8]2)[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 5360545Sodium2×HCID 73761990HCID 73761990, compound

Product 1

HCID 21278098HCID 21278098, compound

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

Sodium (5.6 g) was added portionwise to a suspension of 1-azabicyclo[3.2.2]nonan-4-one oxime hydrochloride (D1) (2.8 g) in amyl alcohol (100 ml) which was heated under reflux. After all the sodium had reacted, the mixture was cooled to 50° and water (20 ml) was added carefully. The aqueous phase was separated and the amyl alcohol was extracted with 5N hydrochloric acid (2×15 ml). The combined acid extract was washed with diethyl ether and the solvent evaporated in vacuo to give 4-amino-1-azabicyclo[3.2.2]nonane hydrochloride. The hydrochloride salt was basified with 40% sodium hydroxide and the aqueous phase was saturated with potassium carbonate, extracted with diethyl ether, dried (Na2SO4) and the solvent evaporated in vacuo to give the title compound (1.4 g, 68%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperaturethe mixture was cooled to 50°
  4. customThe aqueous phase was separated
  5. extractionthe amyl alcohol was extracted with 5N hydrochloric acid (2×15 ml)
  6. extractionThe combined acid extract
  7. washwas washed with diethyl ether
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-9745113d60c942f1839fc5dcfe3a5028
Source dataset
uspto-grants-1989_01
Patent number
US04798829

Reaction notes

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