Hydrochloric Acid → (R)-N-ethyl-N-methylpiperidine-3-carboxamide

HRID 931139Notes

Reaction equation

HRID 931139 reaction equation
[CH2:1]([N:3]([CH3:19])[C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]1)=[O:5])[CH3:2].Cl>C(OCC)C>[CH2:1]([N:3]([CH3:19])[C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117966457(R)-tert-butyl 3-(ethyl(methyl)carbamoyl)piperidine-1-carboxylate

Product 1

HCID 79002271(R)-N-ethyl-N-methylpiperidine-3-carboxamideYield 158.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (R)-tert-butyl 3-(ethyl(methyl)carbamoyl)piperidine-1-carboxylate (1 g, 3.7 mmol) in diethyl ether (10 mL) at 0° C. was added ethereal hydrogen chloride (15 mL). The reaction mixture was warmed to room temperature and was stirred at that temperature for 30 min. The solvent was distilled and the resulting residue was washed with diethyl ether to afford (R)—N-ethyl-N-methylpiperidine-3-carboxamide (1 g). MS (ES+) (M+H) 171.23; LCMS retention time 2.38 min (Method M1).

Workup

  1. distillationThe solvent was distilled
  2. washthe resulting residue was washed with diethyl ether

Sources & evidence

ORD record
ord-1f3db4f37ea44c58a1d6faf2e26df0ab
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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