Water → HCID 22494779, compound

HRID 1816703Notes

Reaction equation

HRID 1816703 reaction equation
[CH:1]1([O:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N[NH:23][C:24]([NH2:26])=[S:25].O.[OH-].[Na+]>C1(C)C=CC=CC=1.FC(F)(F)C(O)=O.C1COCC1.C(OCC)(=O)C>[NH2:26][C:24]1[S:25][C:18]([C:17]2[CH:16]=[CH:15][C:14]([N:11]3[CH2:10][CH2:9][CH:8]([O:7][CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:13][CH2:12]3)=[CH:21][CH:20]=2)=[N:19][N:23]=1

Participants

9

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2723789ThiosemicarbazideHCID 224946954-[4-(Cyclohexyloxy)-1-piperidinyl]benzonitrile

Product 1

HCID 22494779HCID 22494779, compoundYield 71.8%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-(4-cyclohexyloxypiperidin-1-yl)benzonitrile (1.90 g), thiosemicarbazide (0.91 g) in toluene (20 ml) and trifluroacetic acid (10 ml) was stirred at 60-65° C. with stirring for 7 hours. After cooling, the reaction mixture was poured into a mixture of water (100 ml) and ethyl acetate (100 ml) and adjusted to pH 10 with 1N-sodium hydroxide. The mixture was dissolved in a mixture of THF (50 ml) and ethyl acetate (100 ml). The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting precipitate was washed diisopropyl ether and dried in vacuo to give 2-amino-5-[4-[4-(cyclohexyloxy)piperidin-1-yl]phenyl]-1,3,4-thiadiazole (1.72 g).

Workup

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. washThe resulting precipitate was washed diisopropyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-980ceb5bbd5d4b47bfc970718bf8a265
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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