Potassium Carbonate → HCID 69823126, compound

HRID 382811Notes

Reaction equation

HRID 382811 reaction equation
[OH-].[Na+].[Br:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([C@H:12]2[C@H:17]([CH2:18][C:19]([O:21]C)=O)[CH2:16][CH2:15][N:14]([CH3:23])[CH2:13]2)=[CH:6][C:5]=1[O:24][CH3:25].C(=O)([O-])[O-].[K+].[K+].P(Cl)(Cl)(Cl)=O>C(O)C.O>[Br:3][C:4]1[C:5]([O:24][CH3:25])=[CH:6][C:7]2[C@@H:12]3[C@H:17]([CH2:16][CH2:15][N:14]([CH3:23])[CH2:13]3)[CH2:18][C:19](=[O:21])[C:8]=2[C:9]=1[O:10][CH3:11]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide2×HCID 24813Phosphorus oxychlorideHCID 69823083HCID 69823083, compound

Product 1

HCID 69823126HCID 69823126, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2 ml of 1N NaOH solution were added to a solution of 0.726 g (1.87 mmol) of methyl trans-[3-(4-bromo-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate in 3 ml of ethanol and the mixture was stirred at 50° for 30 minutes. The solution was evaporated and the residue was dried in a high vacuum. The thus-obtained sodium salt was suspended in 5 ml of acetonitrile. After the addition of 278 mg (2 mmol) of potassium carbonate the suspension was treated at 0° with 0.913 ml (10 mmol) of phosphorus oxychloride and the mixture was subsequently stirred at 50° for 2 hours. Subsequently, the mixture was poured into 10 ml of water, adjusted to pH=12 with 28% NaOH and extracted three times with 15 ml of ethyl acetate. The organic phase was dried (Na2SO4), filtered and evaporated. Chromatography (silica gel, methylene chloride/methanol 95:5) yielded 0.385 g (58%) of trans-8-bromo-7,9-dimethoxy-2-methyl-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one, which was converted with HCl in methanol into the hydrochloride with m.p. 226-228°.

Workup

  1. customThe solution was evaporated
  2. customthe residue was dried in a high vacuum
  3. stirringthe mixture was subsequently stirred at 50° for 2 hours
  4. extractionextracted three times with 15 ml of ethyl acetate
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-5015429aa39d472b8f0208f57ba3db71
Source dataset
uspto-grants-2001_10
Patent number
US06310208B1

Reaction notes

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