Hydrochloric Acid → HCID 69962380, compound

HRID 429424Notes

Reaction equation

HRID 429424 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:20][CH:19]=3)[C:16]3[C:11](=[CH:12][C:13]([O:32]C)=[CH:14][CH:15]=3)[O:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1.[OH-].[Na+].Cl>O.C(O)C.ClCCl>[OH:32][C:13]1[CH:12]=[C:11]2[C:16]([C@H:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]4[CH2:28][CH2:29][CH2:30][CH2:31]4)=[CH:20][CH:19]=3)[C@H:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:9][O:10]2)=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10176127Pyridinium chlorideHCID 69931180HCID 69931180, compound

Product 1

HCID 69962380HCID 69962380, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
152.5 °C

Procedure

A mixture of (±)-cis-3-(4-fluorophenyl)-7-methoxy-4-(4-(2-pyrrolidinoethoxy)phenyl) -chromane (0.90 g, 2.01 mmol) and anhydrous pyridine hydrochloride (11.60 g, 100 mmol) was heated to 150-155° C. as a melt for 18 hours. The mixture was cooled to room temperature, and the resulting orange coloured wax dissolved in a mixture of water (100 ml), hot ethanol (20 ml) and dichloromethane (150 ml). The aqueous layer was basified to pH 14 by adding 10M sodium hydroxide, then 1M hydrochloric acid was added until pH 8-9. The organic layer was collected and the aqueous layer further extracted with dichloromethane (2×150 ml). The combined organics were washed with saturated sodium chloride, dried over sodium sulfate and evaporated to a dark coloured gum, which was purified by column chromatography on silica gel, with 7% methanol in dichloromethane as eluent, giving the product as a colourless glass. This was dissolved in a minimum of acetone and petroleum ether added to precipitate the product as an amorphous solid, which was vacuum dried.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was collected
  3. extractionthe aqueous layer further extracted with dichloromethane (2×150 ml)
  4. washThe combined organics were washed with saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated to a dark coloured gum, which
  7. customwas purified by column chromatography on silica gel, with 7% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-f4073ec15ce44967b012312179343a4e
Source dataset
uspto-grants-2001_11
Patent number
US06316494B1

Reaction notes

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