Pyridinium chloride → HCID 9953661, compound

HRID 429449Notes

Reaction equation

HRID 429449 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][C@@H:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@H:6]2[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:21][CH:20]=1.Cl.N1C=CC=CC=1>CO.O.ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][C@@H:7]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C@H:6]2[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)=[CH:21][CH:20]=1

Participants

6

Reactant 2

HCID 10176127Pyridinium chlorideHCID 69931466HCID 69931466, compound

Product 1

HCID 9953661HCID 9953661, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of (±)-cis-6-methoxy-3-phenyl-4-(4-(2-pyrrolidinoethoxy)phenyl)chromane (0.34 g, 0.79 mmol) and pyridine hydrochloride (0.91 g, 7.9 mmol) was stirred at 135° C. for 18 h, cooled to room temperature and the resulting dark solid dissolved in a mixture of methanol (10 ml), water (50 ml) and dichloromethane (50 ml). The aqueous layer was separated and further extracted with 4:1 dichloromethane /methanol (50 ml). The organic layers were combined, washed with brine, dried over magnesium sulfate, and evaporated. The product was purified by column chromatography on silica gel 60, with 5% methanol in di-chloromethane as eluent. The resulting gum was dissolved in approximately 1 ml ethanol and then diethylether added. This resulted in the precipitation of the title compound as a partial hydrochloride salt. The solid was dissolved in dichloromethane, washed with sodium hydrogen carbonate solution, brine, dried over magnesium sulfate and evaporated to give the title compound as a pale yellow foam.

Workup

  1. temperaturecooled to room temperature
  2. customThe aqueous layer was separated
  3. extractionfurther extracted with 4:1 dichloromethane /methanol (50 ml)
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe product was purified by column chromatography on silica gel 60, with 5% methanol in di-chloromethane as eluent
  8. dissolutionThe resulting gum was dissolved in approximately 1 ml ethanol
  9. additiondiethylether added

Sources & evidence

ORD record
ord-85c31076790747bf812c3f45a5a28e07
Source dataset
uspto-grants-2001_11
Patent number
US06316494B1

Reaction notes

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