Methyl vinyl ketone → HCID 18621442, compound

HRID 1861784Notes

Reaction equation

HRID 1861784 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[CH3:15][C:16]([CH:18]=[CH2:19])=[O:17]>C(O)(C)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([CH2:19][CH2:18][C:16](=[O:17])[CH3:15])[CH2:11][CH2:12]2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 36998414-(4-Fluoro-benzyl)-piperidine

Product 1

HCID 18621442HCID 18621442, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 4-(4-fluorobenzyl)piperidine (0.50 g, 2.2 mmol) in isopropanol (5 mL) was added methylvinyl ketone (0.25 mL, 3.0 mmol). The resulting solution was stirred at reflux for 1 h then concentrated under reduced pressure to afford the title compound as a pale yellow oil (0.58 g, 99%): 1H NMR (CDCl3) δ1.15-1.35 (m, 2H), 1.38-1.56 (m, 1H), 1.603 (bd, J=12.6 Hz, 2H), 1.894 (t, J=11.7 Hz, 2H), 2.155 (s, 2H), 2.486 (d, J=6.9 Hz, 2H), 2.615 (s, 3H), 2.8-2.9 (m, 2H), 6.9-7.0 (m, 2H), 7.0-7.1 (m, 2H); IR (film) 2928, 1720, 1514, 1219 cm−1.

Workup

  1. temperatureat reflux for 1 h
  2. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-2c404859d5f0418ba0162a150fcf9aa7
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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