Diethyl Ether → N-(4-acetamidophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline hydrochloride

HRID 35232ノート

反応式

HRID 35232 の反応式
Cl.Cl.[NH2:3][C:4]1[CH:26]=[CH:25][C:7]([CH2:8][CH2:9][N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][C:14]([O:22][CH3:23])=[C:15]([O:20][CH3:21])[CH:16]=3)[CH:11]2[CH3:24])=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:34]([Cl:37])(=[O:36])[CH3:35].CCOCC>C(Cl)(Cl)Cl>[ClH:37].[C:34]([NH:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][C:14]([O:22][CH3:23])=[C:15]([O:20][CH3:21])[CH:16]=3)[CH:11]2[CH3:24])=[CH:25][CH:26]=1)(=[O:36])[CH3:35]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 6367Acetyl chloride2 回HCID 8471Triethylamine2 回HCID 3033629Veradoline Hydrochloride

生成物 1

HCID 14230307N-(4-acetamidophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline hydrochloride収率 31.5%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

A stirred suspension of N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline dihydrochloride (11.9 g, 0.03 m) in chloroform (300 ml) under nitrogen at 0° C. was treated with triethylamine (3.5 g, 0.035 m) and then after 5 minutes with acetyl chloride (2.75 g, 0.035 m). The mixture was stirred for 1 hour, retreated with 3.5 g triethylamine and 2.75 g acetyl chloride and stirred an additional hour at 0°. Chloroform (50 ml) and then ether (100 ml) were added and the white solid precipitate collected by filtration, 13.9 g. The solid was dissolved in chloroform (250 ml), filtered to remove insoluble salts and the filtrate washed with cold 10% NaOH (200 ml) and cold water (2×200 ml) and dried over MgSO4. The solvent was carefully evaporated under vacuum at 20°. The residue was dissolved in 200 ml CHCl3 /100 ml ether, cooled in an ice-salt bath and slowly acidified with HCl gas. The precipitated solid was collected by filtration and recrystallized as above, filtering under nitrogen to protect the solid product from moisture and vacuum dried at 85° to give 3.8 g of N-(4-acetamidophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline hydrochloride, m.p. 150°-154°.

後処理

  1. stirringstirred an additional hour at 0°
  2. filtrationthe white solid precipitate collected by filtration, 13.9 g
  3. dissolutionThe solid was dissolved in chloroform (250 ml)
  4. filtrationfiltered
  5. customto remove insoluble salts
  6. washthe filtrate washed with cold 10% NaOH (200 ml) and cold water (2×200 ml)
  7. dry with materialdried over MgSO4
  8. customThe solvent was carefully evaporated under vacuum at 20°
  9. dissolutionThe residue was dissolved in 200 ml CHCl3 /100 ml ether
  10. temperaturecooled in an ice-salt bath
  11. filtrationThe precipitated solid was collected by filtration
  12. customrecrystallized as above,
  13. filtrationfiltering under nitrogen
  14. customdried at 85°

出典と根拠

ORDレコード
ord-aa241c3c5cdb4f63bcc44d11a709c167
出典データセット
uspto-grants-1988_08
特許番号
US04766131

反応ノート

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