Hydrochloric Acid → HCID 86710783, compound

HRID 1400732Notes

Reaction equation

HRID 1400732 reaction equation
Cl.[CH:2](/[C:6]1([CH3:19])[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)=[CH:3]\[CH:4]=[CH2:5].Cl.O1CCOCC1>>[CH:2](/[C:6]1([CH3:19])[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1)=[CH:3]\[CH:4]=[CH2:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 204431481,4-Dioxane hydrochlorideHCID 86710784HCID 86710784, compound

Product 1

HCID 86710783HCID 86710783, compound

Procedure

HCl: A mixture of (E)-tert-butyl 4-(buta-1,3-dien-1-yl)-4-methylpiperidine-1-carboxylate (1.8 g, 7.16 mmol) and 4M HCl/dioxane (8.95 ml, 35.8 mmol) was stirred at room temp for 3 h. Mixture was then concentrated and the solids were triturated with ether/hexane, filtered and dried under high vac to afford (E)-4-(buta-1,3-dien-1-yl)-4-methylpiperidine.HCl (1.2 g, 6.39 mmol, 89% yield) as off-white solid. 1H NMR (500 MHz, DMSO-d6) δ 6.35 (dt, J=16.9, 10.2 Hz, 1H), 6.12 (dd, J=15.7, 10.3 Hz, 1H), 5.78-5.73 (m, 1H), 5.21 (d, J=17.0 Hz, 1H), 5.06 (d, J=10.1 Hz, 1H), 3.14-3.00 (m, 2H), 2.97-2.79 (m, 2H), 1.83-1.69 (m, 2H), 1.64-1.53 (m, 2H), 1.06 (s, 3H). LCMS (M+H)=152.1.

Workup

  1. concentrationMixture was then concentrated
  2. customthe solids were triturated with ether/hexane
  3. filtrationfiltered
  4. customdried under high vac

Sources & evidence

ORD record
ord-0deffbd32097460b93186c5f55685821
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

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