Ethyl bromoacetate → HCID 68735614, compound

HRID 2382195Notes

Reaction equation

HRID 2382195 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][NH:11][CH2:10][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[CH2:9][CH2:10][N:11]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 53853565HCID 53853565, compound

Product 1

HCID 68735614HCID 68735614, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4-(phenyl(4-(trifluoromethyl)phenyl)methyl)piperidine (0.4 g, 1.25 mmol) in MeCN (15 mL) was added triethyl amine (0.45 mL, 3.2 mmol) at rt. After stirring at rt for 10 min, it was cooled to 0° C. and ethyl bromoacetate (0.27 mL, 1.62 mmol) was added dropwise. After stirring at rt for 16 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, 5-10% ethyl acetate in hexane) afforded ethyl 2-(4-(phenyl(4-(trifluoromethyl)phenyl)methyl)piperidin-1-yl)acetate (0.25 g, 52% 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 16 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-f1816915bdfa4db3a4e45f852bdba564
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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