1,4-Dioxane hydrochloride → 4-Allyloxy-4-methylpiperidine hydrochloride

HRID 1481978Notes

Reaction equation

HRID 1481978 reaction equation
[CH2:1]([O:4][C:5]1([CH3:18])[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6]1)[CH:2]=[CH2:3].[ClH:19].O1CCOCC1>>[ClH:19].[CH2:1]([O:4][C:5]1([CH3:18])[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 83206810HCID 83206810, compound

Product 1

HCID 867107764-Allyloxy-4-methylpiperidine hydrochlorideYield 95%

Procedure

A mixture of tert-butyl 4-(allyloxy)-4-methylpiperidine-1-carboxylate (3.10 g, 12.1 mmol) and 4N HCl/dioxane (15 mL, 60.0 mmol) was stirred at rt for 3 h. It was then concentrated in vacuum to obtain 2.2 g (95%) of 4-(allyloxy)-4-methylpiperidine hydrochloride as a light brown solid. 1H NMR (500 MHz, CD3OD) δ 6.02-5.92 (m, 1H), 5.33 (dd, J=17.2, 1.7 Hz, 1H), 5.15 (dd, J=10.6, 1.7 Hz, 1H), 3.96 (dt, J=5.1, 1.6 Hz, 2H), 3.23-3.18 (m, 4H), 2.06 (dd, J=15.3, 2.5 Hz, 2H), 1.77-1.69 (m, 2H), 1.31-1.28 (s, 3H). Free base (brown solid) is obtained by stirring HCl salt with aq Na2CO3 and extracting with DCM.

Workup

  1. concentrationIt was then concentrated in vacuum

Sources & evidence

ORD record
ord-1fec3896dc5f4607a12cf5b631da607b
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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