Hydrogen chloride-ethyl acetate → HCID 22248061, compound

HRID 914869Notes

Reaction equation

HRID 914869 reaction equation
[ClH:1].C(OCC)(=O)C.C(OC([N:15]1[CH2:20][CH2:19][C:18]([OH:30])([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH2:17][CH2:16]1)=O)(C)(C)C>>[ClH:1].[OH:30][C:18]1([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 22247995HCID 22247995, compound

Product 1

HCID 22248061HCID 22248061, compoundYield 100%

Procedure

After adding 5 ml of 4N hydrogen chloride/ethyl acetate to 154 mg of 1-(tert-butoxycarbonyl)-4-hydroxy-4-(2-methylphenoxymethyl)piperidine, the mixture was stirred for 3 hours at room temperature. The solvent was distilled off under reduced pressure to obtain 4-hydroxy-4-(2-methylphenoxymethyl)piperidine hydrochloride (123 mg, 100% yield). The title compound (28 mg, 46% yield) was then obtained in the same manner as Example 1 from 29 mg of 3-tert-butoxypyrazine-2-carboxaldehyde and 41 mg of the 4-hydroxy-4-(2-methylphenoxymethyl)piperidine hydrochloride.

Workup

  1. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-723c53cffed841e1b60c454eb5992623
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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