Hydrochloric Acid → (R)-2-vinylpiperidine hydrochloride

HRID 529524Notes

Reaction equation

HRID 529524 reaction equation
[ClH:1].[CH:2]([C@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1C(OC(C)(C)C)=O)=[CH2:3]>>[ClH:1].[CH:2]([C@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][NH:5]1)=[CH2:3]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 10976755(R)-tert-butyl 2-vinylpiperidine-1-carboxylate

Product 1

HCID 50941258(R)-2-vinylpiperidine hydrochlorideYield 92%

Procedure

A solution of HCl (4 N in 1,4-dioxane, 11.1 mL, 47.9 mmol) was added to an ice bath cooled reaction vessel containing (R)-tert-butyl 2-vinylpiperidine-1-carboxylate (2.53 gm, 12.0 mmol). The reaction mixture was then stirred at rt for 2 hr. The reaction mixture was concentrated and dried under vacuum to give (R)-2-vinylpiperidine hydrochloride (1.62 gm, 11.0 mmol, 92% yield) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 5.89 (1H, ddd, J=17.5, 10.6, 6.6 Hz), 5.50-5.37 (2H, m), 3.74-3.64 (1H, m), 3.38 (1H, d, J=12.6 Hz), 3.09-2.98 (1H, m), 2.04-1.83 (3H, m), 1.74-1.55 (3H, m).

Workup

  1. temperaturecooled
  2. customreaction vessel
  3. concentrationThe reaction mixture was concentrated
  4. customdried under vacuum

Sources & evidence

ORD record
ord-3e345456913b481688965e1bdc318e7e
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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