Piperidine → 3-Hydroxy-2-(p-Diethylaminophenyl-methylidene)-1-Indanone

HRID 1679083ノート

反応式

HRID 1679083 の反応式
[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

参加物

5

反応物 3

HCID 8082PiperidineHCID 671144-(Diethylamino)benzaldehydeHCID 1764483-Hydroxy-1-indanone

生成物 1

HCID 543895683-Hydroxy-2-(p-Diethylaminophenyl-methylidene)-1-Indanone収率 44%

試薬・触媒・溶媒 1

HCID 8005Butyl Chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b2cdb93f7f2442ad9bb0f6f4ee8fa1ac
出典データセット
uspto-grants-1978_03
特許番号
US04078934

反応ノート

読み込み中…