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

HRID 27145

反応式

HRID 27145 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-450ae31ddfe24a7bb4c2f7e67aba0817
出典データセット
uspto-grants-1980_09
特許番号
US04220647

関連ノート

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