Hydrochloric Acid → HCID 69961215, compound

HRID 429418Notes

Reaction equation

HRID 429418 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C@H:7]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)=[CH:25][CH:24]=3)[C@H:8]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH2:9][O:10]2)=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1.[OH-].[Na+].Cl>O.C(O)C.ClCCl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C@H:7]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]4[CH2:33][CH2:34][CH2:35][CH2:36]4)=[CH:25][CH:24]=3)[C@H:8]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=3)[CH2:9][O:10]2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10176127Pyridinium chlorideHCID 70292460HCID 70292460, compound

Product 1

HCID 69961215HCID 69961215, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
152.5 °C

Procedure

A mixture of (±)-cis-7-methoxy-4-(4-(2-pyrrolidinoethoxy)phenyl)-3-(4-(trifluoromethyl)phenyl)chromane (0.30 g, 0.60 mmol) and anhydrous pyridine hydrochloride (3.50 g, 30.3 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 (50 ml), hot ethanol (20 ml) and dichloromethane (100 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 (2×75 ml). The combined organics were washed with saturated sodium chloride, dried over magnesium sulfate and evaporated to a dark coloured gum, which was purified by column chromatography on silica gel, with 6% methanol in dichloromethane as eluent, giving the product as a colourless solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was collected
  3. extractionthe aqueous layer further extracted with dichloromethane (2×75 ml)
  4. washThe combined organics were washed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to a dark coloured gum, which
  7. customwas purified by column chromatography on silica gel, with 6% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-c9903dc175c14c67b97d1035ef4213a0
Source dataset
uspto-grants-2001_11
Patent number
US06316494B1

Reaction notes

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