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

HRID 1828272

Reaction equation

HRID 1828272 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.CCN(C(C)C)C(C)C.[N:30]1([C:36]2[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=2[C:38]#[N:39])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]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:33]1[CH2:32][CH2:31][N:30]([C:36]2[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=2[C:38]#[N:39])[CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 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 DIEA (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-ff2ec1e989874245ab56f51bea23a15c
Source dataset
uspto-grants-2006_06
Patent number
US07057042B2

Linked notes

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