Pyridinium chloride → HCID 67557366, compound

HRID 1604465Notes

Reaction equation

HRID 1604465 reaction equation
Cl.N1C=CC=CC=1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[C@H:24]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)=[CH:27][CH:26]=3)[C:23]3[C:18](=[CH:19][C:20]([O:39]C)=[CH:21][CH:22]=3)[O:17][CH2:16]2)=[CH:11][CH:10]=1>CO.O.C(=O)([O-])O.[Na+]>[OH:39][C:20]1[CH:19]=[C:18]2[C:23]([C@@H:24]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]4[CH2:35][CH2:36][CH2:37][CH2:38]4)=[CH:27][CH:26]=3)[C@H:15]([C:12]3[CH:11]=[CH:10][C:9]([F:8])=[CH:14][CH:13]=3)[CH2:16][O:17]2)=[CH:22][CH:21]=1

Participants

6

Reactant 2

HCID 10176127Pyridinium chlorideHCID 67603239HCID 67603239, compound

Product 1

HCID 67557366HCID 67557366, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of anhydrous pyridine hydrochloride (0.289 g, 2.50 mmol) and (±)-trans-3-(4-fluorophenyl)-7-methoxy-4-(4-(2-pyrrolidinoethoxy)phenyl)-chromane (0.11 g, 0.25 mmol) was heated to 135° C. for 18 h. The resulting dark brown solid was dissolved in a mixture of methanol (10 ml), water (50 ml) and sodium hydrogen carbonate solution (5 ml), and the product extracted into 9:1 dichloromethane /methanol (3×50 ml). The combined extracts were washed with brine, dried over magnesium sulfate and evaporated to an orange gum. The product was purified by column chromatography on silica gel 60, with 5% methanol in dichloromethane eluent, giving the purified product as a colourless wax.

Workup

  1. extractionthe product extracted into 9:1 dichloromethane /methanol (3×50 ml)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to an orange gum
  5. customThe product was purified by column chromatography on silica gel 60, with 5% methanol in dichloromethane eluent
  6. customgiving the purified product as a colourless wax

Sources & evidence

ORD record
ord-45031c87cef34105b660f0973495b22e
Source dataset
uspto-grants-1999_11
Patent number
US05994390

Reaction notes

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