Hydrochloric Acid → 6,7-Dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 35222

反応式

HRID 35222 の反応式
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[C:10]([CH3:16])=[N:9][CH2:8][CH2:7]2.[OH-].[Na+].[BH4-].[Na+].Cl>CO>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[CH:10]([CH3:16])[NH:9][CH2:8][CH2:7]2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 123273036,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline hydrochloride

生成物 1

HCID 103026,7-Dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline収率 100%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of 3,4-dihydro-6,7-dimethoxy-1-methylisoquinoline hydrochloride (47.0 g, 0.229 m) and NaOH (5 g) in absolute methanol (500 ml) was added NaBH4 (34.6 g, 0.917 m) and the mixture stirred for 2 hr (TLC complete) and allowed to stand overnight. The mixture was cooled in an ice bath, treated carefully with 20% HCl until pH 1 was achieved and then heated to 50° for 1 hr. The solvent was then removed on the aspirator and the residue dissolved in 1 liter H2O. The solution was basified to pH 11 with NaOH (20%) and extracted with 3×250 ml CHCl3. The extracts were dried over MgSO4 and evaporated to give 1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline as an oil, 47.6 g (100% yield).

後処理

  1. waitto stand overnight
  2. temperatureThe mixture was cooled in an ice bath
  3. temperatureheated to 50° for 1 hr
  4. customThe solvent was then removed on the aspirator
  5. dissolutionthe residue dissolved in 1 liter H2O
  6. extractionextracted with 3×250 ml CHCl3
  7. dry with materialThe extracts were dried over MgSO4
  8. customevaporated

出典と根拠

ORDレコード
ord-53a5cec0dbdf4e6f814abe1d111d366b
出典データセット
uspto-grants-1988_08
特許番号
US04766131

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