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

HRID 1713094Notes

Reaction equation

HRID 1713094 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.Cl[CH:14]1[CH2:19][N:18]([CH:20]2[CH2:23][CH2:22][CH2:21]2)[CH2:17][CH2:16][NH:15]1.[C:24](N)(=[O:26])[CH3:25].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C.O>[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([CH2:25][C:24]([N:15]1[CH2:16][CH2:17][N:18]([CH:20]3[CH2:23][CH2:22][CH2:21]3)[CH2:19][CH2:14]1)=[O:26])[CH2:7][CH2:6]2

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 225702166-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 668779022-Chloro-(4-cyclobutyl-piperazine) acetamide

Product 1

HCID 574205706-Bromo-2-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 6-bromo-1,2,3,4-tetrahydro-isoquinoline hydrochloride (3.09 g, 12.4 mmol) in acetonitrile (50.0 ml) is added 2-chloro-(4-cyclobutyl-piperazine)-acetamide (2.69 mg, 12.4 mmol, 1.0 eq.), K2CO3 (5.14 g, 37.3 mmol, 3.0 eq.), and NaI (400 mg). The resulting mixture is stirred at rt overnight. Water (40.0 ml) is added to quench the reaction, and then the acetonitrile is evaporated. The residue is extracted with DCM (40 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 flash silica gel chromatography (EtOAc/4% TEA) to give the title compound. MS (+VE) m/z 392.2 (M++1).

Workup

  1. customto quench
  2. customthe reaction
  3. customthe acetonitrile is evaporated
  4. extractionThe residue is extracted with DCM (40 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 flash silica gel chromatography (EtOAc/4% TEA)

Sources & evidence

ORD record
ord-f4e9ceaaaaa54b9a966ecca8ec436657
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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