Sodium Iodide → 6-(Benzyloxy)-2-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinoline

HRID 1713079노트

반응식

HRID 1713079 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][NH:14][CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH:20]1[CH2:25][N:24]([CH:26]2[CH2:29][CH2:28][CH2:27]2)[CH2:23][CH2:22][NH:21]1.[C:30](N)(=[O:32])[CH3:31].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([CH2:31][C:30]([N:21]1[CH2:22][CH2:23][N:24]([CH:26]3[CH2:29][CH2:28][CH2:27]3)[CH2:25][CH2:20]1)=[O:32])[CH2:13][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 106100436-(Benzyloxy)-1,2,3,4-tetrahydroisoquinolineHCID 668779022-Chloro-(4-cyclobutyl-piperazine) acetamide

생성물 1

HCID 574205646-(Benzyloxy)-2-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinoline

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of 6-benzyloxy-1,2,3,4-tetrahydroisoquinoline (1.5 g, 6.26 mmol) in acetonitrile (20.0 ml) is added 2-chloro-(4-cyclobutyl-piperazine)-acetamide (1.36 g, 6.26 mmol, 1.0 eq.), K2CO3 (1.73 g, 12.5 mmol, 2.0 eq.), and NaI (180 mg). The resulting mixture is stirred at rt overnight. Water (20.0 ml) is added to quench the reaction, and then the acetonitrile is evaporated. The residue is extracted with DCM (20 ml×3). The combined organic phase is dried over sodium sulfate, and the solvent is removed under reduced pressure to give a residue that is purified by PTLC (EtOAc/4% TEA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.30-7.44 (5H, m), 6.84-6.94 (1H, m), 6.70-6.80 (2H, 1 m), 5.20 (2H, s), 3.60-3.74 (6H, m), 3.56 (2H, s), 2.62-2.92 (5H, m), 2.22-2.32 (4H, m), 1.60˜2.10 (6H, m); MS (+VE) m/z 420.2 (M++1).

후처리

  1. customto quench
  2. customthe reaction
  3. customthe acetonitrile is evaporated
  4. extractionThe residue is extracted with DCM (20 ml×3)
  5. dry with materialThe combined organic phase is dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customto give a residue that
  8. customis purified by PTLC (EtOAc/4% TEA)

출처 및 근거

ORD 기록
ord-5851f3d8a14a448b84a0ca5c825ece0a
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795262B2

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