Water → HCID 86606819, compound

HRID 1437641Notes

Reaction equation

HRID 1437641 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.[CH3:30][O:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34]O.C(N(C(C)C)CC)(C)C.O>ClCCl>[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]([CH2:34][C:33]2[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=2[O:31][CH3:30])[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 691542-Methoxybenzyl alcoholHCID 81531DiisopropylethylamineHCID 86606807cis-4-[[3,5-Bis(trifluoromethyl)benzyl]oxy]-3-phenylpiperidine hydrochloride

Product 1

HCID 86606819HCID 86606819, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound (0.20 g) obtained in Example 1, 2-methoxybenzyl alcohol (0.075 g) and diisopropylethylamine (0.24 g) in dichloromethane (2 ml), EPPA (0.20 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 saturated ammonium chloride 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:methanol=20:1) to obtain the title compound as colorless oil (0.15 g, 62%).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated ammonium chloride 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:methanol=20:1)

Sources & evidence

ORD record
ord-ad14a605589e4030a95f89334797effd
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

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