Hydrochloric Acid → HCID 178515255, compound

HRID 419732Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][C:11]([OH:37])([C:14]2[N:15](COCC[Si](C)(C)C)[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)C.Cl>>[F:27][C:25]([F:26])([F:28])[C:21]1[CH:20]=[C:19]([C:17]2[N:18]=[C:14]([C:11]3([OH:37])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[NH:15][CH:16]=2)[CH:24]=[CH:23][CH:22]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 66649866HCID 66649866, compound

Product 1

HCID 178515255HCID 178515255, compoundYield 99.6%

Conditions

Temperature: 70 °C

Procedure

To a microwave vial add 4-hydroxy-4-[4-(3-trifluoromethyl-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.453 g; 1.00 equiv; 836.28 μmoles; 453.00 mg), ethanol (5 mL; 85.88 mmoles; 5.00 mL; 3.96 g), and hydrogen chloride (5 mL; 5.00 mmoles; 1N aqueous) and heat to 70° C. in a microwave with stirring on and hold for 4 h. Concentrate the reaction mixture to give 4-[4-(3-Trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-4-ol salt (0.32 g; 1.00 equiv; 832.84 μmoles; 320.00 mg; 99.59% yield).

Workup

concentrationConcentrate the reaction mixture

Sources & evidence

ORD record: ord-d918871e742b4216b269b4871fe426fa
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093383B2

Reaction notes

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