Phosphorus oxychloride → Diproteverine Hydrochloride

HRID 325616ノート

反応式

HRID 325616 の反応式
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:15][CH2:16][NH:17][C:18](=O)[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[C:22]([O:29][CH2:30][CH3:31])[CH:21]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:35])=O>C1C=CC=CC=1>[ClH:35].[CH2:30]([O:29][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[O:26][CH2:27][CH3:28])[CH2:19][C:18]1[C:8]2[C:7](=[CH:6][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[C:10]([O:11][CH:12]([CH3:14])[CH3:13])[CH:9]=2)[CH2:15][CH2:16][N:17]=1)[CH3:31]

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 13276278HCID 13276278、化合物

生成物 1

HCID 3052867Diproteverine Hydrochloride収率 57%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

5.0 g (0.0113 mole) of N-[2-(3,4-diisopropoxyphenyl)-ethyl]-3,4-diethoxyphenylacetamide, 100 ml benzene, and 2.3 g (0.015 mole) of phosphorus oxychloride were introduced successively into a 250 ml 3-necked flask after being passed through an atmosphere of nitrogen. The mixture was heated under reflux with stirring over a period of 2 hours, 70 ml of solvent removed by distillation, 30 ml of ethanol, 1 ml of 12 N hydrochloric acid added and the bulk of solvent removed by distillation under reduced pressure. The residue obtained was washed several times with ether, taken up again in solution in 15 ml of ethanol, and 120 ml of ether added slowly. The slowly precipitated product was dried to give 2.93 g of 1-(3'4'-diethoxybenzyl)-6,7-diisopropoxy-3,4-dihydroisoquinoline hydrochloride. Yield=57%, m.p. 187° C.

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. custom70 ml of solvent removed by distillation, 30 ml of ethanol, 1 ml of 12 N hydrochloric acid
  4. additionadded
  5. customthe bulk of solvent removed by distillation under reduced pressure
  6. customThe residue obtained
  7. washwas washed several times with ether
  8. addition120 ml of ether added slowly
  9. customThe slowly precipitated product was dried

出典と根拠

ORDレコード
ord-98447d22c84d4111800f65ac7ebe57b4
出典データセット
uspto-grants-1984_04
特許番号
US04442108

反応ノート

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