Phosphorus oxychloride → Diproteverine Hydrochloride

HRID 325616노트

반응식

HRID 325616 반응식
[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]

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 13276278HCID 13276278, 화합물

생성물 1

HCID 3052867Diproteverine Hydrochloride수율 57%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-98447d22c84d4111800f65ac7ebe57b4
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04442108

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