Hydrochloric Acid → Ethyl 3-piperidin-4-ylbenzoate hydrochloride

HRID 385293Notes

Reaction equation

HRID 385293 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:25].O1CCOCC1>>[ClH:25].[CH2:23]([O:22][C:20](=[O:21])[C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:15]=1)[CH3:24]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57880576Tert-butyl 4-[3-(ethoxycarbonyl)phenyl]piperidine-1-carboxylate

Product 1

HCID 66973363Ethyl 3-piperidin-4-ylbenzoate hydrochloride

Procedure

To a solution of 4-(3-ethoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (10.55 g, 31.64 mmol) was added a solution of 4M HCl in dioxane (79 mL, 316.41 mmol)) at RT. After stirring overnight at RT, the solvent was evaporated under reduce pressure. The resulting yellowish viscous oil was triturated with diethylether, and filtered to give 3-piperidin-4-yl-benzoic acid ethyl ester hydrochloride salt (8.53 g, quant.). 1H-NMR (400 MHz, d6-DMSO): δ=1.81-1.86 (t, 3H), 1.91-1.98 (m, 3H), 2.50-2.52 (m, 1H (overlap with DMSO), 2.95-3.05 (m, 2H), 3.32-3.39 (m, 2H), 4.31-4.39 (q, 2H), 7.49-7.52 (m, 2H), 7.81-7.83 (m, 2H), 9.5 (br, 2H). MS: m/z=234 ((M-HCl)+1).

Workup

  1. customthe solvent was evaporated
  2. customThe resulting yellowish viscous oil was triturated with diethylether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-70b2011d002748578b50fbae8c00f5b9
Source dataset
uspto-grants-2013_02
Patent number
US08367844B2

Reaction notes

Loading…