Piperidine → HCID 54065145, compound

HRID 258518Notes

Reaction equation

HRID 258518 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([CH:7]=[CH:8][CH:9]=[O:10])=[CH:5][CH:4]=1)#[N:2].O[C:14]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=1[C:22](=[O:27])[CH2:23]S(C)=O.N1CCCCC1>C1(C)C=CC=CC=1>[CH3:21][O:20][C:19]1[C:14]2[O:10][C:9]([CH:8]=[CH:7][C:6]3[CH:11]=[CH:12][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)=[CH:23][C:22](=[O:27])[C:15]=2[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 124350051-(2-Hydroxy-3-methoxyphenyl)-2-(methanesulfinyl)ethan-1-oneHCID 54292473HCID 54292473, compound

Product 1

HCID 54065145HCID 54065145, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7.85 g of 4-cyanocinnamaldehyde (U.S. Pat. No. 2,993,834), 11.4 g of 2'-hydroxy-3'-methoxy-2-(methylsulfinyl)acetophenone, 250 ml of toluene, and 0.5 ml of piperidine was refluxed for 3 hrs. The mixture was chilled, and the crystalline ppt. filtered, and recrystallized from toluene, mp. 274°-75°; yield 7 g (46%); λ max mμ (ε) 222 (20,600), 328 (42,500); ν max 745 (m), 845 (m), 1060 (m), 1275 (m), 1570 (m), 1595 (m), 1655 (ms), 2230 (m) cm-1.

Workup

  1. temperatureThe mixture was chilled
  2. filtrationfiltered
  3. customrecrystallized from toluene, mp. 274°-75°

Sources & evidence

ORD record
ord-c58993c4b1924283a61e6d9dd90771ac
Source dataset
uspto-grants-1977_07
Patent number
US04033845

Reaction notes

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