Piperidine → HCID 53686284, compound

HRID 258519Notes

Reaction equation

HRID 258519 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:14])=[C:6]([C:8](=[O:13])[CH2:9]S(C)=O)[CH:7]=1.[C:15]([C:17]1[CH:26]=[CH:25][C:20]([CH:21]=[CH:22][CH:23]=O)=[CH:19][CH:18]=1)#[N:16].N1CCCCC1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][C:23]([CH:22]=[CH:21][C:20]3[CH:19]=[CH:18][C:17]([C:15]#[N:16])=[CH:26][CH:25]=3)=[CH:9][C:8](=[O:13])[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 218282451-(5-Bromo-2-hydroxyphenyl)-2-(methanesulfinyl)ethan-1-oneHCID 54292473HCID 54292473, compound

Product 1

HCID 53686284HCID 53686284, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3.9 g of 5'-bromo-2'-hydroxy-2-(methylsulfinyl)acetophenone, 2.2 g of p-cyanocinnamaldehyde, 50 ml of toluene and 0.1 ml of piperidine was refluxed for 4 hrs. The mixture was chilled, and the precipitate was filtered and recystallized from DMF, mp 275°-76° ; yield 1 g (20%); λ max mμ (ε) 223 (22,700), 273 (12,900), 330 (41,000); ν max 840 (m), 980 (m), 1280 (m), 1640 (m), 1660 (ms), 2240 (m) cm-1.

Workup

  1. temperaturewas refluxed for 4 hrs
  2. temperatureThe mixture was chilled
  3. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-4affa26ec73c419ea8251ec720d93359
Source dataset
uspto-grants-1977_07
Patent number
US04033845

Reaction notes

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