Water → HCID 86606827, compound

HRID 1437676Notes

Reaction equation

HRID 1437676 reaction equation
Cl.[F:2][C:3]([F:29])([F:28])[C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN(CC)CC.[CH3:37][N:38]=[C:39]=[S:40].O>C(#N)C>[F:29][C:3]([F:2])([F:28])[C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:23]=1)[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:39](=[S:40])[NH:38][CH3:37])[CH2:11][C@H:10]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11167Methyl isothiocyanateHCID 86606807cis-4-[[3,5-Bis(trifluoromethyl)benzyl]oxy]-3-phenylpiperidine hydrochloride

Product 1

HCID 86606827HCID 86606827, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the compound (0.20 g) obtained in Example 1 and Et3N (0.16 ml) in acetonitrile (10 ml), methyl isothiocyanate (0.083 g) was added, and the reaction mixture was stirred at room temperature for 14 hours. The reaction mixture was poured into water, and then the product was extracted with ethyl acetate. The organic layer was washed with an aqueous 10% citric acid solution and saturated brine, dried, and then the solvent was evaporated under reduced pressure. The obtained residue was isolated and purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain the title compound as colorless oil (0.22 g, 99%).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous 10% citric acid solution and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was isolated
  6. custompurified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-d20a14854ac04369b0d96793507a8c0e
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

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