Ethyl Acetate → 2-[4-(1-Benzothien-2-ylmethyl)-1-piperazinyl]benzonitrile

HRID 2377674

Reaction equation

HRID 2377674 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10]O.CS(OS(C)(=O)=O)(=O)=O.CC(=O)OCC.[N:27]1([C:33]2[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=2[C:35]#[N:36])[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][N:30]1[CH2:29][CH2:28][N:27]([C:33]2[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=2[C:35]#[N:36])[CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81560Methanesulfonic anhydrideHCID 2735875N-(2-Cyanophenyl)piperazineHCID 27763352-(Hydroxymethyl)benzo[b]thiophene

Product 1

HCID 99969482-[4-(1-Benzothien-2-ylmethyl)-1-piperazinyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 8A (150 mg 0.9 mmol), methane sulfonic anhydride (159 mg, 0.9 mmol), and D1 EA (475 μL 2.7 mmol) were combined. After stirring, 2-(1-piperazinyl)benzonitrile (181 mg, 1.0 mmol) in 2 ml DCM was also combined and stirred at room temperature for 18 hours. The mixture was concentrated and the residue was taken up in hot methanol. The methanol was filtered and the filter cake washed with cold methanol to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 2.69 (m, 4H) 3.04 (s, 4H) 3.76 (m, 4H) 3.86 (s, 1H) 6.74 (m, 2H) 7.29 (m, 3H) 7.75 (m, 1H); (ESI) m/z 334 (M+H)+.

Workup

  1. stirringstirred at room temperature for 18 hours
  2. concentrationThe mixture was concentrated
  3. filtrationThe methanol was filtered
  4. washthe filter cake washed with cold methanol

Sources & evidence

ORD record
ord-c9a658dc3dd743c4a7da7ed15e88db60
Source dataset
uspto-grants-2008_12
Patent number
US07470691B2

Linked notes

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