Hydrochloric Acid → 4-Methyl-5-piperazin-1-yl-thiazole dihydrochloride

HRID 1775326Notes

Reaction equation

HRID 1775326 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[N:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]1.[ClH:20].O1CCOCC1.CO>C(OCC)C>[ClH:20].[ClH:20].[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 312751,4-DioxaneHCID 89825959tert-Butyl 4-(4-methylthiazol-5-yl)piperazine-1-carboxylate

Product 1

HCID 898254774-Methyl-5-piperazin-1-yl-thiazole dihydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of tert-butyl 4-(4-methylthiazol-5-yl)piperazine-1-carboxylate (265 mg, 0.935 mmol) in diethyl ether (10 mL) was added HCl (4N in dioxane, 4.5 mL, 18 mmol) after which a precipitate formed immediately. 1,4-Dioxane (5 mL) was added to dissolve the precipitate. The mixture was stirred at room temperature for three days after which additional HCl (4N in dioxane, 5 mL, 20 mmol) and methanol (5 ml) was added. Stirring was continued for another day, the precipitate formed was collected by filtration, washed with diethylether and dried under reduced pressure to yield 208 mg of a yellow solid (0.812 mmol, 87%). MS (ESI) m/z=184.1 [M+1]+.

Workup

  1. customformed immediately
  2. dissolutionto dissolve the precipitate
  3. additionwas added
  4. waitwas continued for another day
  5. customthe precipitate formed
  6. filtrationwas collected by filtration
  7. washwashed with diethylether
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-5b41760c37294ae0b59e3045507caffe
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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