Hydrochloric Acid → Ethyl 1-methylpiperidine-4-carboxylate

HRID 1012122Notes

Reaction equation

S(Cl)(Cl)=O.Cl.[CH3:6][N:7]1[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=[O:14])[CH2:9][CH2:8]1.[CH2:16](O)[CH3:17]>>[CH2:16]([O:14][C:13]([CH:10]1[CH2:11][CH2:12][N:7]([CH3:6])[CH2:8][CH2:9]1)=[O:15])[CH3:17]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 24386Thionyl Chloride

HCID 27369391-Methylpiperidine-4-carboxylic acid

Product 1

HCID 11062856Ethyl 1-methylpiperidine-4-carboxylateYield 100%

Procedure

Thionyl chloride (0.80 ml, 11 mmol) was added dropwise to a suspension of the HCl salt of 1-methyl-piperidine-4-carboxylic acid (1.80 g, 10 mmol) in ethanol (25 ml). The reaction mixture was stirred at ambient temperature overnight, then reduced in vacuo and dried by azeotrope with toluene (×3) to give 1-methyl-piperidine-4-carboxylic acid ethyl ester as a colourless solid (1.7 g, 100%). (LC/MS: Rt 0.41, [M+H]+ 172.08).

Workup

dry with materialdried by azeotrope with toluene (×3)

Sources & evidence

ORD record: ord-6b8e66650fdc489cb0a94deef9d12298
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977477B2

Reaction notes

Loading…