Hydrochloric Acid → 4-Phenylpiperidine-4-carboxylic acid, compound with toluene-p-sulphonic acid

HRID 216026

Reaction equation

HRID 216026 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[C:17]1([C:11]2([C:14]([OH:16])=[O:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 7369171-((Tert-butoxy)carbonyl)-4-phenylpiperidine-4-carboxylic acid

Product 1

HCID 192594-Phenylpiperidine-4-carboxylic acid, compound with toluene-p-sulphonic acidYield 109.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-(tert-Butoxycarbonyl)-4-phenylpiperidine-4-carboxylic acid (1.0 g, 3.3 mmol) was treated with 4 N HCl in dioxane (20 mL) for 2 hours at room temperature. The product was isolated by filtration to provide the title compound (0.74 g, 93%) as a white solid. MS (ES+) [M+H]+=206.

Workup

  1. customThe product was isolated by filtration

Sources & evidence

ORD record
ord-1df7985a55a04ddfa276f21ffbc22a18
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Linked notes

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