Sodium Hydroxide → HCID 86741954, compound

HRID 986796Notes

Reaction equation

HRID 986796 reaction equation
[Cl:1]([O-])(=O)(=O)=O.[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH2:14][CH2:15][CH2:16][CH:17]2[N+:22]=1[CH2:21][CH2:20][CH2:19][CH2:18]2.[OH-].[Na+]>CCOCC>[ClH:1].[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C@H:13]1[N:22]2[C@@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15599075HCID 15599075, compound

Product 1

HCID 86741954HCID 86741954, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 3.78 g sample (0.01 mole) of 4-(2-bromophenyl)-1,2,3,6,7,8,9,9a-octahydroquinolizinium perchlorate, the product of Example 5d, was partitioned between ether and sodium hydroxide solution. The ether layer was washed with brine, dried (K2CO3) and the ether evaporated under reduced pressure. The residue (2.0 g) was hydrogenated in 25 mL of glacial acetic acid over 50 mg of PtO2 at 50 psi in a Parr shaker. After 15 minutes, the hydrogen uptake was complete. The catalyst was removed by filtration and the solvent was evaporated under reduced pressure. The residue was partitioned between ether and sodium hydroxide and dried (K2CO3). The residue was taken up in ether and ethereal hydrogen chloride added. The precipitate was recrystallized from 2-propanol-ether to give 1.09 g (33% yield) of the title compound as a white solid, mp 242°-246° C.

Workup

  1. washThe ether layer was washed with brine
  2. dry with materialdried (K2CO3)
  3. customthe ether evaporated under reduced pressure
  4. customThe catalyst was removed by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was partitioned between ether and sodium hydroxide
  7. dry with materialdried (K2CO3)
  8. additionethereal hydrogen chloride added
  9. customThe precipitate was recrystallized from 2-propanol-ether

Sources & evidence

ORD record
ord-3fe7335e76af4667a30269e98388d138
Source dataset
uspto-grants-1987_12
Patent number
US04716172

Reaction notes

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