Hydrochloric Acid → HCID 118115293, compound

HRID 1050583Notes

Reaction equation

HRID 1050583 reaction equation
[CH:1]1([N:4]2[CH2:8][CH2:7][N:6]([C@@H:9]3[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]3)[C:5]2=[O:22])[CH2:3][CH2:2]1.[ClH:23]>O1CCOCC1>[ClH:23].[CH:1]1([N:4]2[CH2:8][CH2:7][N:6]([C@@H:9]3[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]3)[C:5]2=[O:22])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118114583HCID 118114583, compound

Product 1

HCID 118115293HCID 118115293, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(R)-tert-Butyl 3-(3-cyclopropyl-2-oxoimidazolidin-1-yl)piperidine-1-carboxylate (391) (3.0 g, 9.7 mmol) was treated with commercial 4N HCl in dioxane at RT to afford (R)-1-cyclopropyl-3-(piperidin-3-yl)imidazolidin-2-one hydrochloride (392) (2.05 g, 86%) as a light brown solid after concentration in vacuo. Proton NMR (DMSO-d6): δ 9.37 (1H, s), 8.99 (1H, s), 3.89-3.82 (1H, m), 3.64-3.57 (1H, m), 3.28-3.18 (4H, m), 3.11-3.03 (1H, m), 2.97-2.87 (1H, m), 2.77-2.67 (1H, m), 2.44-2.29 (1H, m), 1.89-1.80 (1H, m), 1.75-1.64 (3H, m), 0.81-0.36 (4H, m) ppm.

Sources & evidence

ORD record
ord-48e1b551a5ec49f4b6c460284686cf9d
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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