1-Butanol → 1-(N-benzyloxycarbonyl-3,4,5-trimethoxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 27147

반응식

HRID 27147 반응식
C(O[CH:4](OCC)[CH2:5][N:6]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1)C.[ClH:32].[OH:33][C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][C:42]=1[OH:43])[CH2:37][CH2:38][NH2:39].C(O)CCC>O>[ClH:32].[CH2:22]([O:21][C:19]([N:6]([CH2:5][CH:4]1[C:40]2[C:36](=[CH:35][C:34]([OH:33])=[C:42]([OH:43])[CH:41]=2)[CH2:37][CH2:38][NH:39]1)[C:7]1[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 3

HCID 2631-ButanolHCID 65340Dopamine HydrochlorideHCID 20460529N-benzyloxycarbonyl-3,4,5-trimethoxyanilinoacetaldehyde diethyl acetal

생성물 1

HCID 204605511-(N-benzyloxycarbonyl-3,4,5-trimethoxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride수율 70.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

N-benzyloxycarbonyl-3,4,5-trimethoxyanilinoacetaldehyde diethyl acetal (21 g) and 3,4-dihydroxyphenethylamine hydrochloride (8.3 g) were added to a mixture of n-butyl alcohol (210 ml) and water (30 ml) and then the mixture was refluxed for 11 hours in a stream of nitrogen. In the course of the reaction, amounts of the above-mentioned acetal (2.1 g, 2.1 g and 4.2 g) were added to the mixture after 5 hours, 6 hours and 7 hours, respectively, from the beginning of the reaction, respectively. The reaction mixture was concentrated to dryness under reduced pressure and the residue was washed with ether and acetone to give 1-(N-benzyloxycarbonyl-3,4,5-trimethoxyanilinomethyl)-6,7-dihydroxy,1,2,3,4-tetrahydroisoquinoline hydrochloride (16.3 g). The product was recrystallized from a mixed solvent of ethanol and ether to give a pure product, mp 197° to 199° C. (dec).

후처리

  1. temperaturethe mixture was refluxed for 11 hours in a stream of nitrogen
  2. additionwere added to the mixture after 5 hours, 6 hours and 7 hours
  3. customrespectively, from the beginning of the reaction
  4. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  5. washthe residue was washed with ether and acetone

출처 및 근거

ORD 기록
ord-a43635fea12b4c809e92f1044b1ffa83
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04220647

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