Pyridinium chloride → HCID 13851353, compound

HRID 979164Notes

Reaction equation

HRID 979164 reaction equation
[Br:1][C:2]1[C:7]2[O:8][CH2:9][C@@H:10]3[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][C@@H:11]3[C:6]=2[CH:5]=[C:4]([O:17]C)[CH:3]=1.Cl.N1C=CC=CC=1>O.[OH-].[Na+]>[Br:1][C:2]1[C:7]2[O:8][CH2:9][C@@H:10]3[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][C@@H:11]3[C:6]=2[CH:5]=[C:4]([OH:17])[CH:3]=1

Participants

5

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13851351HCID 13851351, compound

Product 1

HCID 13851353HCID 13851353, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 0.5 g (±)[4aR*,10bS*]-7-bromo-1,3,4,4a,5,10b-hexahydro-9-methoxy-2-methyl-2H-[1]benzopyrano[4,3-c]pyridine and 5 g pyridine hydrochloride is heated under nitrogen at 200° for 20 minutes. The cooled reaction mixture is dissolved in water and basified with 6N NaOH. The aqueous phase is extracted with three 25 ml portions of CH2Cl2, the extracts are dried over Na2SO4, filtered, concentrated under reduced pressure, and flash chromatographed with methylene chloride/ammonia saturated methanol (10:1) to afford the title compound; m.p. HCl salt 259°-262°.

Workup

  1. temperatureis heated under nitrogen at 200° for 20 minutes
  2. customThe cooled reaction mixture
  3. extractionThe aqueous phase is extracted with three 25 ml portions of CH2Cl2
  4. dry with materialthe extracts are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure, and flash
  7. customchromatographed with methylene chloride/ammonia saturated methanol (10:1)

Sources & evidence

ORD record
ord-6ff5be320c004493a1949ce5722594cd
Source dataset
uspto-grants-1987_05
Patent number
US04666916

Reaction notes

Loading…