Formaldehyde → HCID 18767195、化合物

HRID 481163ノート

反応式

HRID 481163 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=[O:18])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.[CH2:19]=O.[ClH:21].[CH3:22][NH:23][CH3:24]>C(#N)C>[ClH:21].[CH2:11]([CH:10]([CH2:22][N:23]([CH3:19])[CH3:24])[C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 112071953'-METHOXY-3-PHENYLPROPIOPHENONE

生成物 1

HCID 18767195HCID 18767195、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

28 g (0.12 mole) of 1-(3-methoxyphenyl)-3-phenylpropan-1-one were dissolved in 200 ml of acetonitrile, following which 11.3 g (0.12 mole) of the iminium salt of paraformaldehyde and dimethylamine hydrochloride were added under a nitrogen atmosphere. The reaction mixture was then heated for one hour at 60° C. and afterwards cooled to 20° C. The product partially precipitates on stirring overnight. The solvent was removed in vacuo and the crude product was dissolved in water. Sodium bicarbonate was added to the aqueous solution until the pH was 8 and the solution was then extracted three times with ether. The ether extracts were combined, dried over sodium sulfate and the ether was distilled off. The (2RS)-2-benzyl-3-dimethylamino-1-(3-methoxyphenyl)-propan-1-one was dissolved in 100 ml of methyl ethyl ketone and ethereal HCl solution was added until the pH was 1. The resultant precipitate was suction filtered, washed with ether and dried in vacuo; 2-benzyl-3-dimethylamino-1-(3-methoxyphenyl)-propan-1-one hydrochloride was obtained in a yield of 33.0 g (83%) with a melting point of 130° C.

後処理

  1. additionwere added under a nitrogen atmosphere
  2. temperatureafterwards cooled to 20° C
  3. customThe product partially precipitates
  4. customThe solvent was removed in vacuo
  5. dissolutionthe crude product was dissolved in water
  6. additionSodium bicarbonate was added to the aqueous solution until the pH was 8
  7. extractionthe solution was then extracted three times with ether
  8. dry with materialdried over sodium sulfate
  9. distillationthe ether was distilled off
  10. dissolutionThe (2RS)-2-benzyl-3-dimethylamino-1-(3-methoxyphenyl)-propan-1-one was dissolved in 100 ml of methyl ethyl ketone
  11. additionethereal HCl solution was added until the pH was 1
  12. filtrationfiltered
  13. washwashed with ether
  14. customdried in vacuo

出典と根拠

ORDレコード
ord-2d3de82f3d8c44daadd047fa31c35ac5
出典データセット
uspto-grants-2003_11
特許番号
US06653508B2

反応ノート

読み込み中…