2-Chlorobenzaldehyde → HCID 1109367, compound

HRID 2083190Notes

Reaction equation

HRID 2083190 reaction equation
CN1CCC(=[O:8])CC1.ClC1C=CC=CC=1C=O.[OH-].[K+].[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]=[C:28]1[CH2:33][C:32](=[CH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[Cl:41])[CH2:31][N:30]([CH3:42])[C:29]1=O>C(O)C>[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]=[C:28]1[C:33](=[O:8])[C:32](=[CH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[Cl:41])[CH2:31][N:30]([CH3:42])[CH2:29]1

Participants

6

Reactant 4

HCID 69962-ChlorobenzaldehydeHCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 54287285HCID 54287285, compound

Product 1

HCID 1109367HCID 1109367, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 11.3 g. (0.1 mole) of 1-methyl-4-piperidinone and 28 g. (0.2 mole) of o-chlorobenzaldehyde in 220 ml. of ethanol is treated with 11 g. (0.17 mole) of 85% KOH. The temperature rises to 34° and after approximately 2 minutes a solid begins to separate. After stirring for 30 minutes the yellow solid is filtered, washed with water, and air-dried to yield 31.6 g. of yellow, 3,5-bis[(2-chlorophenyl)methylene]-1-methyl-piperidinone; m.p. 148°-150°.

Workup

  1. customto separate
  2. filtrationis filtered
  3. washwashed with water
  4. customair-dried
  5. customto yield 31.6 g

Sources & evidence

ORD record
ord-feef4f2a400c4e5a8e2e613c932379bf
Source dataset
uspto-grants-1978_04
Patent number
US04085102

Reaction notes

Loading…