Piperidine → 2-[[4-(Diethylamino)phenyl]methylene]-2,3-dihydro-3-hydroxy-1H-inden-1-one

HRID 1679083Notes

Reaction equation

HRID 1679083 reaction equation
[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)[CH3:2].[OH:14][CH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[CH2:16]1.N1CCCCC1>ClCCCC>[OH:24][CH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](=[O:14])[C:16]1=[CH:8][C:7]1[CH:10]=[CH:11][C:4]([N:3]([CH2:12][CH3:13])[CH2:1][CH3:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 671144-(Diethylamino)benzaldehydeHCID 1764483-Hydroxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 543895682-[[4-(Diethylamino)phenyl]methylene]-2,3-dihydro-3-hydroxy-1H-inden-1-oneYield 44%

Reagents, catalysts & solvents 1

HCID 8005Butyl ChlorideSolvent

Procedure

A mixture of 56.6 g.(0.32 mole) of p-diethylaminobenzaldehyde, 47.36 g. (0.32 mole) of 3-hydroxy-1-indanone and 7 ml. of piperidine was then heated with magnetic stirring to 80°-100° C. for 1.5 hours (the mixture is a melt at the reaction temperature). The mixture was cooled in ice water, 90 ml. of 1-chlorobutane and seed was added. The product tended to come out as a gum; the solution was therefore heated, cooled (seeded) and muddy brown solid separated. The product was collected by filtration and the brown solid washed until bright orange; 43.62 g. 44% yield, m.p. 139°-141°, m.p. recrystallized material (1-chlorobutane) 142°-143° C. An extra 11% yield was obtained through concentration and refiltration of the filtrate; the latter fraction washed up as cleanly as the first. The IR spectrum and elemental analysis are those expected of the titled merocyanine derivative.

Workup

  1. additionA mixture of 56.6 g
  2. temperaturethe solution was therefore heated
  3. temperaturecooled (seeded) and muddy brown solid
  4. customseparated
  5. filtrationThe product was collected by filtration
  6. washthe brown solid washed until bright orange
  7. custom44% yield, m.p. 139°-141°, m.p. recrystallized material (1-chlorobutane) 142°-143° C
  8. customAn extra 11% yield was obtained through concentration and refiltration of the filtrate
  9. washthe latter fraction washed up as cleanly as the first

Sources & evidence

ORD record
ord-b2cdb93f7f2442ad9bb0f6f4ee8fa1ac
Source dataset
uspto-grants-1978_03
Patent number
US04078934

Reaction notes

Loading…