Hydrochloric Acid → Methyl 4-allylpiperidine-4-carboxylate

HRID 1864913Notes

Reaction equation

HRID 1864913 reaction equation
Cl.[CH2:2]([C:5]1([C:18]([OH:20])=[O:19])[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6]1)[CH:3]=[CH2:4].[CH3:21]O>>[CH2:2]([C:5]1([C:18]([O:20][CH3:21])=[O:19])[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1)[CH:3]=[CH2:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 224691981-((Tert-butoxy)carbonyl)-4-(prop-2-en-1-yl)piperidine-4-carboxylic acid

Product 1

HCID 66972977Methyl 4-allylpiperidine-4-carboxylate

Procedure

HCl (g) was bubbled through a solution of 4-allyl-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid [Jiang et al. (2004) Bioorg. Med. Chem. Lett. 14, 3675-3678] (6.50 g, 24.1 mmol,) in MeOH (200 mL). The solution was heated at reflux for 16 h and then concentrated in vacuo to give the title compound as the hydrochloride salt. MS: m/z=184(M+1).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-579f99272cb24ce7bd0cd6eb01689b4c
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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