Hydrogen chloride-ethyl acetate → (3R)-3-(Methoxymethyl)-piperidine HCl

HRID 1012242Notes

Reaction equation

HRID 1012242 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:9][CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1.[ClH:17].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:17].[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:9][CH2:8][CH2:7][NH:6][CH2:5]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 58826553tert-butyl (R)-3-methoxymethylpiperidine-1-carboxylate

Product 1

HCID 66795288(3R)-3-(Methoxymethyl)-piperidine HCl

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (R)-3-methoxymethylpiperidine-1-carboxylate (13.00 g, 56.6 mmol) in ethyl acetate (26 ml) was added 4N HCl-ethyl acetate solution (26 ml), and the mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure to give (R)-3-methoxymethylpiperidine hydrochloride as a crude product. A mixed solvent (100 ml) of hexane:ethyl acetate=1:4 was added to the obtained solid, and the mixture was stirred. The solid was collected by filtration to give (R)-3-methoxymethylpiperidine hydrochloride (7.82 g, yield 84%).

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b8ad4a45926745dd861b1e22cbff51dc
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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