1,4-Dioxane hydrochloride → HCID 117603298, compound

HRID 1481968Notes

Reaction equation

HRID 1481968 reaction equation
[CH2:1]([C:5]1([CH3:18])[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6]1)[CH2:2][CH:3]=[CH2:4].Cl.O1CCOCC1>>[CH2:1]([C:5]1([CH3:18])[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1)[CH2:2][CH:3]=[CH2:4]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 117603758HCID 117603758, compound

Product 1

HCID 117603298HCID 117603298, compound

Procedure

A mixture of tert-butyl 4-(but-3-en-1-yl)-4-methylpiperidine-1-carboxylate (3.5 g, 13.81 mmol) and 4M HCl/dioxane (17.27 ml, 69.1 mmol) was stirred at room temp for 3 h. Mixture was then concentrated and dried under high vac to afford 4-(but-3-en-1-yl)-4-methylpiperidine.HCl (2.6 g, 13.70 mmol, 99% yield) as off-white solid. 1H NMR (500 MHz, DMSO-d6) δ 5.83 (ddt, J=17.0, 10.3, 6.6 Hz, 1H), 5.05 (dq, J=17.1, 1.7 Hz, 1H), 5.00-4.80 (m, 1H), 3.11-2.90 (m, 5H), 2.05-1.90 (m, 2H), 1.56-1.42 (m, 5H), 1.38-1.26 (m, 2H), 0.95 (s, 3H). LCMS (M+H)=154.1.

Workup

  1. concentrationMixture was then concentrated
  2. customdried under high vac

Sources & evidence

ORD record
ord-39d85b4043d74d5a9c52b0531e41640e
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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