Piperidine → HCID 25233560, compound

HRID 404681

Reaction equation

HRID 404681 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(C(C)C)C(C)C)C>CC#N>[F:13][C:10]1[CH:11]=[CH:12][C:7]([CH:2]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:3]([O:5][CH3:6])=[O:4])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 12717580Methyl 2-bromo-2-(4-fluorophenyl)acetate

Product 1

HCID 25233560HCID 25233560, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 2-bromo-2-(4-fluorophenyl)acetate (538 mg, 2.18 mmol) was dissolved in CH3CN (6.6 ml) and piperidine (258 μl, 2.61 mmol) and N-ethyl-N-isopropylpropan-2-amine (456 μl, 2.61 mmol) were added sequentially. The solution was stirred at room temperature for 3 hours, then the solvent was evaporated and the crude was purified with flash chromatography (Petroleum ether/EtOAc=9/1) to collect methyl 2-(4-fluorophenyl)-2-(piperidin-1-yl)acetate (320 mg, 58.5% yield) as a colourless oil.

Workup

  1. customthe solvent was evaporated
  2. customthe crude was purified with flash chromatography (Petroleum ether/EtOAc=9/1)

Sources & evidence

ORD record
ord-3ea66e4b826b45e89e165860d7a6f754
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Linked notes

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