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

HRID 1713079ノート

反応式

HRID 1713079 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5851f3d8a14a448b84a0ca5c825ece0a
出典データセット
uspto-grants-2010_09
特許番号
US07795262B2

反応ノート

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