Hydrochloric Acid → 4-[4-[5-(2-Hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidinium chloride

HRID 38724Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[O:12][N:11]=[C:10]([C:13]2[N:14]=[C:15]([CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)[S:16][CH:17]=2)[CH2:9]1.[ClH:31]>ClCCl.O1CCOCC1>[Cl-:31].[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[O:12][N:11]=[C:10]([C:13]2[N:14]=[C:15]([CH:18]3[CH2:23][CH2:22][NH2+:21][CH2:20][CH2:19]3)[S:16][CH:17]=2)[CH2:9]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 4-{4-[5-(2-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.70 g) in dichloromethane was added dropwise, at 0° C. a 4 molar solution of hydrogen chloride (4.0 eq.) in 1,4-dioxane. 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 4-{4-[5-(2-hydroxy-phenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidinium chloride (1.45 g).

Workup

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

Sources & evidence

ORD record: ord-a3539106471a4d9d8ca292faef93c0fb
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524743B2

Reaction notes

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