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

HRID 27145

반응식

HRID 27145 반응식
C(O[CH:4](OCC)[CH2:5][N:6]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)C.[ClH:27].[OH:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][C:37]=1[OH:38])[CH2:32][CH2:33][NH2:34].C(O)CCC>O>[ClH:27].[CH2:17]([O:16][C:14]([N:6]([CH2:5][CH:4]1[C:35]2[C:31](=[CH:30][C:29]([OH:28])=[C:37]([OH:38])[CH:36]=2)[CH2:32][CH2:33][NH:34]1)[C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=1)=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

5

반응물 3

HCID 2631-ButanolHCID 65340Dopamine HydrochlorideHCID 20460580N-benzyloxycarbonyl-p-toluidinoacetaldehyde diethyl acetal

생성물 1

HCID 204605901-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride수율 63.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

N-benzyloxycarbonyl-p-toluidinoacetaldehyde diethyl acetal (6 g) and 3,4-dihydroxyphenethylamine hydrochloride (2.5 g) were added to a mixture of n-butyl alcohol (60 ml) and water (8.5 ml) and then the mixture was refluxed for 9.5 hours in a stream of nitrogen. In the course of the reaction, the above-mentioned acetal (0.6 g) was twice added to the mixture, after 5 hours and after 7.5 hours from the beginning of the reaction. The reaction mixture was concentrated and the residue was washed with ether and dissolved in hot water (300 ml). After the insoluble material was filtered off, the filtrate was washed with ethyl acetate and treated with activated charcoal. The aqueous layer was concentrated to dryness to give amorphous 1-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3.8 g), mp 125° C. (dec).

후처리

  1. temperaturethe mixture was refluxed for 9.5 hours in a stream of nitrogen
  2. customIn the course of the reaction
  3. concentrationThe reaction mixture was concentrated
  4. washthe residue was washed with ether
  5. dissolutiondissolved in hot water (300 ml)
  6. filtrationAfter the insoluble material was filtered off
  7. washthe filtrate was washed with ethyl acetate
  8. additiontreated with activated charcoal
  9. concentrationThe aqueous layer was concentrated to dryness

출처 및 근거

ORD 기록
ord-450ae31ddfe24a7bb4c2f7e67aba0817
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04220647

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