Water → HCID 44307162, compound

HRID 2210697Notes

Reaction equation

HRID 2210697 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]([F:36])([F:35])[C:11]1[CH:12]=[C:13]([CH2:21][O:22][C@H:23]2[CH2:28][CH2:27][CH2:26][NH:25][C@H:24]2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([N:25]1[CH2:26][CH2:27][CH2:28][C@H:23]([O:22][CH2:21][C:13]2[CH:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:16]=[C:11]([C:10]([F:9])([F:35])[F:36])[CH:12]=2)[C@@H:24]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1328463-((3,5-Bis(trifluoromethyl)phenyl)methyloxy)-2-phenylpiperidine

Product 1

HCID 44307162HCID 44307162, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

Benzyl bromide (0.134 ml) was added to a mixture of (+)-cis-3-((3,5-bis(trifluoromethyl)phenyl)methyloxy)-2-phenyl piperidine (prepared from the hydrochloride salt, Example 5) (0.5 g) and potassium carbonate (0.468 g) in N,N-dimethylformamide (2 ml) and the mixture stirred at 23° C. for 2.5 h. Water (20 ml) was added and the mixture extracted with ethyl acetate (3×15 ml). The combined organic extracts were washed with water (1×10 ml) and brine (1×10 ml) then dried (K2CO3) and concentrated to leave an oil. Purification on silica gel eluting with hexanes-ethyl acetate (19:1 then 9:1 then 4:1 then 1:1) provided the title compound as a solid, m.p.=89°-93° C. Found: C, 66.11; H, 5.25; N, 2.81. Calcd. for C27H25NOF6 ; C, 65.71; H, 5.11; N, 2.84%.

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×15 ml)
  2. washThe combined organic extracts were washed with water (1×10 ml) and brine (1×10 ml)
  3. dry with materialthen dried (K2CO3)
  4. concentrationconcentrated
  5. customto leave an oil
  6. customPurification on silica gel eluting with hexanes-ethyl acetate (19:1

Sources & evidence

ORD record
ord-1ea261ec167d4d74b8feec18582589e5
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

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