Methyl iodide → 6,8-Dichloro-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline

HRID 48249ノート

反応式

HRID 48249 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N+:7](C)([CH3:13])[CH2:6][CH:5]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.FC(F)(F)C([O-])=O.CI>Cl.CC(C)=O.C(N(C(C)C)CC)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

7

反応物 3

HCID 6328Methyl iodide2 回HCID 84468TrifluoroacetateHCID 121125146,8-Dichloro-2,2-dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinolinium

生成物 1

HCID 223868076,8-Dichloro-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 313Hydrochloric Acid溶媒HCID 81531Diisopropylethylamine溶媒

実験手順

6,8-Dichloro-2,2-dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinolinium, trifluoroacetate; Intermediate 4 (100 mg) was dissolved in the form of its hydrochloride in acetone (1 ml) in the presence of diisopropylethylamine (58 μl). Methyl iodide (38 μl) was then added dropwise with stirring. The mixture was then stirred at room temperature for two hours and subsequently left to stand for 62 h. Since the reaction was still not complete, further methyl iodide (38 μl) was added and the mixture was heated to reflux. After two hours, the reaction mixture was cooled and then concentrated to dryness in a rotary evaporator. The residue was purified by preparative HPLC on RP-18 with acetonitrile/water (0.05% TFA), and the pure fractions were combined. The acetonitrile was stripped off and then the aqueous residue was freeze dried. 132 mg of the desired product were obtained as a solid. (Rt=4.22 min (method A); MS (Cl+): 306.0).

後処理

  1. stirringThe mixture was then stirred at room temperature for two hours
  2. waitsubsequently left
  3. temperaturethe mixture was heated to reflux
  4. waitAfter two hours
  5. temperaturethe reaction mixture was cooled
  6. concentrationconcentrated to dryness in a rotary evaporator
  7. customThe residue was purified by preparative HPLC on RP-18 with acetonitrile/water (0.05% TFA)
  8. customdried

出典と根拠

ORDレコード
ord-10a7641c12c744048014d48f2b6c6477
出典データセット
uspto-grants-2004_03
特許番号
US06703405B2

反応ノート

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