2-Chloro-N,N-dimethylethylamine → Ethanamine, 2-((1,3-dihydro-6-methyl-4-(phenylmethyl)furo(3,4-c)pyridin-7-yl)oxy)-N,N-dimethyl-, dihydrochloride

HRID 1156398ノート

反応式

HRID 1156398 の反応式
[CH2:1]([C:8]1[C:13]2[CH2:14][O:15][CH2:16][C:12]=2[C:11]([OH:17])=[C:10]([CH3:18])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[H-].[Na+].[H][H].[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27][Cl:28]>CS(C)=O>[ClH:28].[ClH:28].[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27][O:17][C:11]1[C:12]2[CH2:16][O:15][CH2:14][C:13]=2[C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:9][C:10]=1[CH3:18]

参加物

7

反応物 5

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 5360545SodiumHCID 129409064-Benzyl-1,3-dihydro-6-methylfuro(3,4-c)pyridin-7-olHCID 178418361HCID 178418361、化合物

生成物 1

HCID 3052096Ethanamine, 2-((1,3-dihydro-6-methyl-4-(phenylmethyl)furo(3,4-c)pyridin-7-yl)oxy)-N,N-dimethyl-, dihydrochloride

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

12.1 g (50 mmoles) of 4-benzyl-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-ol (compare Example 8, stage 1) are suspended in 40 ml of dry dimethylsulfoxide and converted to the sodium salt by adding 1.75 g (60 mmoles) of sodium hydride (85% strength in oil) at 20° C. When the evolution of hydrogen has ceased, 8.1 g (75 mmoles) of freshly distilled β-dimethylaminoethyl chloride are added dropwise, and the mixture is left to stand for 15 hours at 10° C. The dimethylsulfoxide is then distilled off under greatly reduced pressure. The residue is taken up in methylene chloride, the salts and the unconverted pyridinol are washed out with dilute sodium hydroxide solution and the organic phase is dried and concentrated under reduced pressure. The residue is converted, by means of dilute hydrochloric acid, into the hydrochloride, which is recrystallized from an ethanol/ether mixture. 10.0 g of 4-benzyl-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-yl β-dimethylaminoethyl ether bis-hydrochloride, of melting point 213°-214° C., are obtained.

後処理

  1. waitthe mixture is left
  2. distillationThe dimethylsulfoxide is then distilled off under greatly reduced pressure
  3. washthe salts and the unconverted pyridinol are washed out with dilute sodium hydroxide solution
  4. customthe organic phase is dried
  5. concentrationconcentrated under reduced pressure
  6. customis recrystallized from an ethanol/ether mixture

出典と根拠

ORDレコード
ord-e93878e4b4a9491bbb326f85a1f09264
出典データセット
uspto-grants-1982_06
特許番号
US04335241

反応ノート

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