Hydrochloric Acid → HCID 66584582, compound

HRID 409944Notes

Reaction equation

HRID 409944 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[O:14][N:13]=[C:12]([C:15]2[N:16]=[C:17]([CH:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)[S:18][CH:19]=2)[CH2:11]1)(=[O:3])[CH3:2].[ClH:33]>O1CCOCC1>[ClH:33].[NH:23]1[CH2:24][CH2:25][CH:20]([C:17]2[S:18][CH:19]=[C:15]([C:12]3[CH2:11][CH:10]([C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[C:1](=[O:3])[CH3:2])[O:14][N:13]=3)[N:16]=2)[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66584972Tert-butyl 4-{4-[5-(2-acetylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

Product 1

HCID 66584582HCID 66584582, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 4-{4-[5-(2-acetylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (500 mg) in 1,4-dioxane (5 ml) was added dropwise, at 0° C., a 4 molar solution of hydrogen chloride in 1,4-dioxane (4.2 ml). The reaction mixture was stirred at 0° C. and then gradually warmed to room temperature. After stirring overnight, the solvent and excess hydrogen chloride were removed. This gave 1-(2-{3-[2-(piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl)ethanone hydrochloride (430 mg).

Workup

  1. temperaturegradually warmed to room temperature
  2. stirringAfter stirring overnight
  3. customthe solvent and excess hydrogen chloride were removed

Sources & evidence

ORD record
ord-1c919881bbef4a9b88c9d9a2bc22e152
Source dataset
uspto-grants-2014_06
Patent number
US08759527B2

Reaction notes

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