Hydrochloric Acid → 1-[4-(Pyridin-4-ylmethoxy)-[1,2,5]thiadiazol-3-yl]-piperazine, dihydrochloride salt

HRID 907523Notes

Reaction equation

HRID 907523 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:18]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[N:17][S:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:27]>O1CCOCC1.CCOC(C)=O>[ClH:27].[ClH:27].[N:24]1[CH:25]=[CH:26][C:21]([CH2:20][O:19][C:18]2[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[N:15][S:16][N:17]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 590139624-[4-(Pyridin-4-ylmethoxy)-[1,2,5]thiadiazol-3-yl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 1317291731-[4-(Pyridin-4-ylmethoxy)-[1,2,5]thiadiazol-3-yl]-piperazine, dihydrochloride saltYield 96%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

4-[4-(pyridin-4-ylmethoxy)-[1,2,5]thiadiazol-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (6.9 g, 18.3 mmol) was dissolved in 4M HCl in dioxane (200 mL) and stirred at room temperature for 2 h. The resulting suspension was diluted with EtOAc and the solids filtered, washed with EtOAc, and dried under high vacuum to give 6.15 g (96%) of 1-[4-(pyridin-4-ylmethoxy)-[1,2,5]thiadiazol-3-yl]-piperazine, dihydrochloride salt. 1H NMR (D2O) 8.59 (d, 2H), 7.92 (d, 2H), 5.66 (s, 2H), 3.66 (m, 4H), 3.26 (m, 4H) ppm. LC-MS (MH+)=278.

Workup

  1. filtrationthe solids filtered
  2. washwashed with EtOAc
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-53f3e8400c0d4a96a3953c3adb01f49b
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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