Formaldehyde → 2-Dimethylaminomethyl-4-(phenethyl)-cyclohexanone hydrochloride

HRID 2392757ノート

反応式

HRID 2392757 の反応式
[CH2:1]([CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C=O.Cl.[CH3:19][NH:20][CH3:21].[CH3:22][Si](C)(C)[Cl:24].O>C(O)(=O)C.CC(=O)CC>[ClH:24].[CH3:19][N:20]([CH2:22][CH:13]1[CH2:14][CH:9]([CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:10][CH2:11][C:12]1=[O:15])[CH3:21]

参加物

7

反応物 4

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 189804984-(Phenethyl)-cyclohexanoneHCID 86753056Chlorotrimethylsilane water

生成物 1

HCID 189804162-Dimethylaminomethyl-4-(phenethyl)-cyclohexanone hydrochloride収率 58%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6569Methyl Ethyl Ketone溶媒

反応条件

温度
105 °C

実験手順

20.2 g (0.1 mole) of compound (47), 1.5 g (0.05 mole) paraformaldehyde and 4.07 g (0.05 mole) dimethylamine hydrochloride were dissolved in 40 ml acetic acid and heated in a bath at 105° C. for 20 minutes with stirring. The acetic acid was subsequently distilled off under vacuum, and the residue was dissolved in 100 ml water and extracted with ether. The aqueous phase was adjusted to a pH of 11 with aqueous sodium hydroxide solution and the Mannich base was extracted with dichloromethane. After drying and removal of the solvent by distillation, 17.5 g of the base of compound (47) were obtained, and were taken up in 2-butanone. 17.2 g of compound (48) were obtained in a yield of 58% theoretical by the subsequent addition of trimethylchlorosilane/water.

後処理

  1. distillationThe acetic acid was subsequently distilled off under vacuum
  2. dissolutionthe residue was dissolved in 100 ml water
  3. extractionextracted with ether
  4. extractionthe Mannich base was extracted with dichloromethane
  5. customAfter drying
  6. customremoval of the solvent
  7. distillationby distillation, 17.5 g of the base of compound (47)
  8. customwere obtained

出典と根拠

ORDレコード
ord-fbd5dd582a2d4472a6e62c032229dca5
出典データセット
uspto-grants-1998_09
特許番号
US05801201

反応ノート

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