Hydrochloric Acid → HCID 59438437, compound

HRID 2177539Notes

Reaction equation

HRID 2177539 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([S:33][CH3:34])[C:4]=1[C:5]([NH:7][C:8]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH:12]([O:14]COC)[CH2:11][N:10]([CH3:18])[CH2:9]1)=[O:6].Cl>CO>[OH:14][CH:12]1[CH2:11][N:10]([CH3:18])[CH2:9][C:8]([NH:7][C:5](=[O:6])[C:4]2[C:25]([S:33][CH3:34])=[CH:26][C:27]([C:29]([F:30])([F:31])[F:32])=[CH:28][C:3]=2[O:2][CH3:1])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59438419HCID 59438419, compound

Product 1

HCID 59438437HCID 59438437, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 17 mg (0.0341 mmol) rac-2-methoxy-N-(5-methoxymethoxy-1-methyl-3-phenyl-piperidin-3-yl)-6-methylsulfanyl-4-trifluoromethyl-benzamide in 0.5 ml methanol were added 102 ul (0.102 mmol) of an aqueous 1N HCl solution. The mixture was stirred at room temperature for 30 minutes and then in a 65° C. oil bath for 24 hours. The solvent was removed in vacuo. The residue was taken in water. The aqueous layer was basified with a 2M Na2CO3 solution and extracted 3 times with dichloromethane. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 8 mg (52%) of the title compound as a white solid. MS (m/e): 455.2 (MH+).

Workup

  1. waitin a 65° C. oil bath for 24 hours
  2. customThe solvent was removed in vacuo
  3. extractionextracted 3 times with dichloromethane
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%)

Sources & evidence

ORD record
ord-7f40a6e07e964eac9babdd1699cef43d
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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