Hydrochloric Acid → Methyl 4-methylpiperidine-4-carboxylate hydrochloride

HRID 1713901Notes

Reaction equation

HRID 1713901 reaction equation
[ClH:1].[CH3:2][C:3]1([C:16]([O:18][CH3:19])=[O:17])[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][CH2:4]1>O1CCOCC1>[ClH:1].[CH3:2][C:3]1([C:16]([O:18][CH3:19])=[O:17])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 463183881-tert-Butyl 4-methyl 4-methylpiperidine-1,4-dicarboxylate

Product 1

HCID 56773794Methyl 4-methylpiperidine-4-carboxylate hydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4M HCl in dioxane (25 mL) was added to 1-tert-butyl 4-methyl 4-methylpiperidine-1,4-dicarboxylate (5.28 g, 20.55 mmol) at ambient temperature. The reaction mixture was allowed to stir at ambient temperature for 5 hrs. The solvent was removed under reduced pressure and ether was added to the residue and the suspension was filtered and dried to give the title compound as a white solid (3.82 g, 19.72 mmol, 96%); 1H NMR δ 1.12 (s, 3H), 1.53-1.60 (m, 2H), 1.99-2.04 (m, 2H), 2.76-2.82 (m, 2H), 3.07-3.12 (m, 2H), 3.61 (s, 3H), 8.72 (s, 1H); MS m/e MH+-157

Workup

  1. customThe solvent was removed under reduced pressure and ether
  2. additionwas added to the residue
  3. filtrationthe suspension was filtered
  4. customdried

Sources & evidence

ORD record
ord-b6f6cd94b6774729997a7af8b5649b64
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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