Water → HCID 22492875, compound

HRID 1816697Notes

Reaction equation

HRID 1816697 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1.N[NH:24][C:25]([NH2:27])=[S:26].O.[OH-].[Na+]>C1(C)C=CC=CC=1.FC(F)(F)C(O)=O.C1COCC1.CO.C(OCC)(=O)C>[NH2:27][C:25]1[S:26][C:21]([C:18]2[CH:19]=[CH:20][C:15]([N:12]3[CH2:13][CH2:14][CH:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH2:10][CH2:11]3)=[CH:16][CH:17]=2)=[N:22][N:24]=1

Participants

10

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2723789ThiosemicarbazideHCID 22492869HCID 22492869, compound

Product 1

HCID 22492875HCID 22492875, compoundYield 352.4%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(5-methoxypentyloxy)-N-(4-cyanophenyl)piperidine (294 mg) and thiosemicarbazide (0.68 g) in toluene (20 ml) and trifluoroacetic acid (10 ml) was stirred at 60-65° C. for 7 hours. After cooling, the reaction mixture was poured into a mixture of water (100 ml) and ethyl acetate (200 ml) and adjusted to pH 10 with 1N-sodium hydroxide. The mixture was dissolved in a mixture of THF (50 ml) and methanol (10 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 with isopropyl ether and dried in vacuo to give 2-amino-5-[4-[4-(5-methoxypentyloxy)piperidin-1-yl]phenyl]-1,3,4-thiadiazole (1.29 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 with isopropyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-fea67edb078846caba97c474c5bb02e4
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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