Piperidine → HCID 43227153, compound

HRID 632726Notes

Reaction equation

HRID 632726 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[CH:6]=1)=[O:4].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>C(Cl)(Cl)Cl>[F:11][C:7]1[CH:6]=[C:5]([C:3](=[O:4])[CH2:2][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 27374513-Fluorophenacyl bromide

Product 1

HCID 43227153HCID 43227153, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2-bromo-1-(3-fluoro-phenyl)-ethanone (5.0 g; 23.04 mmol; 1.0 eq.), piperidine (2.30 ml; 23.04 mmol; 1.0 eq.) and DIEA (4.89 ml; 27.65 mmol; 1.20 eq.) in CHCl3 (100 mL) was heated for reflux overnight. The mixture was partitioned between CHCl3 and saturated aqueous NaHCO3. The separated organic layer was dried over MgSO4, filtered and concentrated. The residue was purified through flash chromatography on silica gel to afford the title compound. LC-MS: 222 (M+H).

Workup

  1. temperaturewas heated
  2. temperaturefor reflux overnight
  3. customThe mixture was partitioned between CHCl3 and saturated aqueous NaHCO3
  4. dry with materialThe separated organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified through flash chromatography on silica gel

Sources & evidence

ORD record
ord-2da19c8413074eaa81c75190146f05c6
Source dataset
uspto-grants-2016_04
Patent number
US09321760B2

Reaction notes

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