Water → HCID 57966226, compound

HRID 420556Notes

Reaction equation

HRID 420556 reaction equation
Cl.[Cl:2][C:3]1[CH:26]=[CH:25][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23]Cl)[CH:18]=4)[CH2:12][CH2:11]3)[S:9][C:5]=2[CH:4]=1.[C-:27]#[N:28].[Na+].O.C(OCC)(=O)C>CN(C)C=O>[Cl:2][C:3]1[CH:26]=[CH:25][C:6]2[N:7]=[C:8]([N:10]3[CH2:11][CH2:12][N:13]([CH2:16][C:17]4[CH:18]=[C:19]([CH2:23][C:27]#[N:28])[CH:20]=[CH:21][CH:22]=4)[CH2:14][CH2:15]3)[S:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 66658169HCID 66658169, compound

Product 1

HCID 57966226HCID 57966226, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

The mixture of 6-chloro[4-(3-chloromethylbenzyl)piperazine-1-yl]benzothiazole monohydrochloride (0.50 g; 1.27 mmol) and sodium cyanide (0.19 g; 3.82 mmol) in anhydrous N,N-dimethylformamide (5 ml) were stirred at 40° C. for 1.5 hours. After cooling, water and ethyl acetate were added to the reaction solution. The organic layer was separated and washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure and the percipitate was washed with diisopropyl ether to give {3-[[4-(6-chlorobenzothiazole-2-yl)piperazine-1-yl]methyl]phenyl}acetonitrile as pale blackish brown crystal (0.35 g; 72%).

Workup

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated under reduced pressure
  6. washthe percipitate was washed with diisopropyl ether

Sources & evidence

ORD record
ord-c73550e2fed0417d8f52ed5bf7ebb0a9
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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