Sodium Iodide → 1-(4-cyclobutyl-piperazin-1-yl)-2-(7-methoxy-1,2,4,5-tetrahydro-benzo[D]azepin-3-yl)-ethanone

HRID 1713090Notes

Reaction equation

HRID 1713090 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.Cl[CH:15]1[CH2:20][N:19]([CH:21]2[CH2:24][CH2:23][CH2:22]2)[CH2:18][CH2:17][NH:16]1.[C:25](N)(=[O:27])[CH3:26].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C.O>[CH:21]1([N:19]2[CH2:18][CH2:17][N:16]([C:25](=[O:27])[CH2:26][N:9]3[CH2:10][CH2:11][C:5]4[CH:4]=[C:3]([O:2][CH3:1])[CH:13]=[CH:12][C:6]=4[CH2:7][CH2:8]3)[CH2:15][CH2:20]2)[CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 138533487-Methoxy-2,3,4,5-tetrahydro-1h-3-benzazepineHCID 668779022-Chloro-(4-cyclobutyl-piperazine) acetamide

Product 1

HCID 574206121-(4-cyclobutyl-piperazin-1-yl)-2-(7-methoxy-1,2,4,5-tetrahydro-benzo[D]azepin-3-yl)-ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 7-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (177 mg, 1.0 mmol) in acetonitrile (5.0 ml) is added 2-chloro-(4-cyclobutyl-piperazine)-acetamide (216 mg, 1.0 mmol, 1.0 eq.), K2CO3 (376 mg, 2.0 mmol, 2.0 eq.) and NaI (30 mg). The resulting mixture is stirred at rt overnight. Water (10.0 ml) is added to quench the reaction, and the acetonitrile is evaporated. The residue is extracted with DCM (10 ml×3). The combined extracts are dried over sodium sulfate, and the solvent is removed under reduced pressure. The resulting residue is purified by PTLC (EtOAc/4% TEA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 6.99 (1H, d), 6.60˜6.66 (2H, m), 3.77 (3H, s), 3.60˜3.73 (4H, m), 3.26 (2H, s), 2.80˜3.00 (4H, m), 2.58˜2.73 (5H, m), 2.25˜2.40 (4H, m), 1.65˜2.10 (6H, m); MS (+VE) m/z 358.4 (M++1).

Workup

  1. customto quench
  2. customthe reaction
  3. customthe acetonitrile is evaporated
  4. extractionThe residue is extracted with DCM (10 ml×3)
  5. dry with materialThe combined extracts are dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe resulting residue is purified by PTLC (EtOAc/4% TEA)

Sources & evidence

ORD record
ord-96002983f1e740629ffe38e356625425
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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