Hydrochloric Acid → HCID 21584328, compound

HRID 583257Notes

Reaction equation

HRID 583257 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]2[CH2:8][CH:9]3[N:14]([C:15](=O)[C:6]=2[CH:5]=1)[CH2:13][CH2:12][CH2:11][CH2:10]3)([O-:3])=[O:2].B.[ClH:20]>C1COCC1.C(O)C>[ClH:20].[N+:1]([C:4]1[CH:18]=[CH:17][C:7]2[CH2:8][CH:9]3[N:14]([CH2:15][C:6]=2[CH:5]=1)[CH2:13][CH2:12][CH2:11][CH2:10]3)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 21584299HCID 21584299, compound

Product 1

HCID 21584328HCID 21584328, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 8-nitro-1,3,4,6,11,11a-hexahydro-2H-benzo[b]quinolizin-6-one (4.18 g, 17.0 mmol) in anhydrous THF (50 ml) was added 1.0M borane in THF (50 ml). The reaction mixture was heated at reflux for 18 h. After cooling to room temperature, the excess borane was quenched by the addition of methanol and 6M hydrochloric acid (6 ml) and the solution was heated for 2 h. The solvent was removed in vacuo and the residue was taken up in water. The resulting solution was basified with sodium hydroxide and extracted twice with dichloromethane. The dried (magnesium sulfate) organic phase was concentrated to give an oil which was immediately taken up in ethanol (60 ml). Hydrochloric acid in ethanol was added until the solution was distinctly acidic and the solution was stirred for several hours at ambient temperature. The precipitate was collected, washed with ethanol, and air-dried to give the title compound as a white solid (3.03 g, 70%), m.p. 245-7° C. (dec.).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. customthe excess borane was quenched by the addition of methanol and 6M hydrochloric acid (6 ml)
  4. temperaturethe solution was heated for 2 h
  5. customThe solvent was removed in vacuo
  6. extractionextracted twice with dichloromethane
  7. dry with materialThe dried (magnesium sulfate) organic phase
  8. concentrationwas concentrated
  9. customto give an oil which
  10. customThe precipitate was collected
  11. washwashed with ethanol
  12. customair-dried

Sources & evidence

ORD record
ord-e15bece9873640148144c9c7a316b83a
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

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