Hydrochloric Acid → Racemic cis (4-methyl-piperidin-3-yl)-carbamic acid methyl ester hydrochloride

HRID 1257625Notes

Reaction equation

HRID 1257625 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@H:11]([CH3:14])[C@H:10]([NH:15][C:16]([O:18][CH3:19])=[O:17])[CH2:9]1)=O)(C)(C)C.[ClH:20]>O1CCOCC1>[ClH:20].[CH3:19][O:18][C:16](=[O:17])[NH:15][C@H:10]1[C@@H:11]([CH3:14])[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131730629Racemic cis 3-methoxycarbonylamino-4-methyl-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 131730630Racemic cis (4-methyl-piperidin-3-yl)-carbamic acid methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of racemic cis 3-methoxycarbonylamino-4-methyl-piperidine-1-carboxylic acid tert-butyl ester (2.00 g, 7.35 mmol) in 4 M HCl in dioxane (40 mL) was stirred at ambient temperature for 1 hour then concentrated under vacuum. The resulting residue was azeotroped with DCM to afford 1.7 g (quant.) of racemic cis (4-methyl-piperidin-3-yl)-carbamic acid methyl ester hydrochloride. LCMS (Method I, ESI): RT=0.34 min, m+H=173.4.

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe resulting residue was azeotroped with DCM

Sources & evidence

ORD record
ord-efb1a35eee0b453290614e2a583c1a34
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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