Ethyl bromoacetate → Ethyl 2-(3-(phenyl(4-(trifluoromethyl)phenyl)methyl)piperidin-1-yl)acetate

HRID 2382188Notes

Reaction equation

HRID 2382188 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:8]2[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C(OCC)(=O)C>CC#N.CCCCCC>[C:1]1([CH:7]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)[CH:8]2[CH2:13][CH2:12][CH2:11][N:10]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 687345103-(Phenyl(4-(trifluoromethyl)phenyl)methyl)piperidine

Product 1

HCID 68733022Ethyl 2-(3-(phenyl(4-(trifluoromethyl)phenyl)methyl)piperidin-1-yl)acetateYield 48%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

To a solution of 3-(phenyl(4-(trifluoromethyl)phenyl)methyl)piperidine (1.0 g, 3.13 mmol) in MeCN (10 mL) was added triethyl amine (1.3 mL, 9.4 mmol) at rt. After stirring at rt for 15 min, it was cooled to 0° C. and ethyl bromoacetate (0.62 g, 3.71 mmol) was added dropwise. After stirring at rt for 6 h, the solvent was removed under vacuum and the residue was diluted with water, extracted with ethyl acetate, the combined organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to afforded the crude product. Column chromatography (SiO2, 10-15% ethyl acetate in hexane) afforded ethyl 2-(3-(phenyl(4-(trifluoromethyl)phenyl)methyl)piperidin-1-yl)acetate (0.6 g, 48% yield) as a pale yellow solid. MS (ESI, pos. ion) m/z: 406 (M+1).

Workup

  1. temperatureit was cooled to 0° C.
  2. stirringAfter stirring at rt for 6 h
  3. customthe solvent was removed under vacuum
  4. additionthe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customto afforded the crude product

Sources & evidence

ORD record
ord-5c6dd2905dc942e399d098d95120614c
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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