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

HRID 48249노트

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HRID 48249 반응식
[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

참가 물질

7

반응물 3

HCID 6328Methyl iodide2회HCID 84468TrifluoroacetateHCID 121125146,8-Dichloro-2,2-dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinolinium

생성물 1

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

시약·촉매·용매 3

HCID 180Acetone용매HCID 313Hydrochloric Acid용매HCID 81531Diisopropylethylamine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-10a7641c12c744048014d48f2b6c6477
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703405B2

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