Sodium Bicarbonate → HCID 19927832, compound

HRID 22293Notes

Reaction equation

HRID 22293 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[CH2:14][CH:13]([CH2:15][CH:16]4[CH2:21][CH2:20][N:19]([CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH2:18][CH2:17]4)[C:12](=[O:29])[C:8]=3[NH:9][C:10]=2[CH:11]=1.C(=O)(O)[O-].[Na+]>Br>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[CH2:14][CH:13]([CH2:15][CH:16]4[CH2:21][CH2:20][N:19]([CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH2:18][CH2:17]4)[C:12](=[O:29])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 19927857HCID 19927857, compound

Product 1

HCID 19927832HCID 19927832, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1,2,3,4-tetrahydro-6-methoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]cyclopent[b]indol-3-one (200 mg, 0.51 mmol) and 48% HBr (30 ml) was heated to 110° C. for 3.5 hours. The reaction mixture was allowed to cool and saturated sodium bicarbonate was added until pH 8. The mixture obtained was filtered and the aqueous filrate was extracted with ethanol and the resulting mixture was filtered. Aqueous Na2S2O4 was added to the ethanolic filtrate and the light brown solution obtained was concentrated. The residue was partitioned between water and boiling ethyl acetate. The organic layer was combined and washed with water, brine, dried, filtered and concentrated. The residue was purified through silica gel column chromatography to give the title compound as a yellow solid (100 mg). The material was recrystallized from ethanol to give a pale yellow solid, mp. 250°-252° C.; Anal. Calc. for C24H26N2O2.0.25H2O: C, 76.06; H, 7.05; N, 7.39; ound: C, 76.27; H, 6.67; N, 7.36.

Workup

  1. temperatureto cool
  2. customThe mixture obtained
  3. filtrationwas filtered
  4. extractionthe aqueous filrate was extracted with ethanol
  5. filtrationthe resulting mixture was filtered
  6. additionAqueous Na2S2O4 was added to the ethanolic filtrate
  7. customthe light brown solution obtained
  8. concentrationwas concentrated
  9. customThe residue was partitioned between water
  10. washwashed with water, brine
  11. customdried
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-92c794217443468fa0ca037712c24c9d
Source dataset
uspto-grants-1995_06
Patent number
US05428043

Reaction notes

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