Hydrochloric Acid → 4-(piperidin-4-yloxy)pyridin-2(1H)-one hydrochloride

HRID 705501Notes

Reaction equation

HRID 705501 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:4][NH:3]1.[ClH:22]>>[ClH:22].[NH:12]1[CH2:13][CH2:14][CH:9]([O:8][C:6]2[CH:5]=[CH:4][NH:3][C:2](=[O:1])[CH:7]=2)[CH2:10][CH2:11]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67366878Tert-butyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

Product 1

HCID 899072924-(piperidin-4-yloxy)pyridin-2(1H)-one hydrochlorideYield 100%

Procedure

A 100 mL round bottom flask was charged with tert-butyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate (1.36 g, 4.62 mmol) and hydrogen chloride (37% in H2O, 4 mL). The mixture was stirred at room temperature for 15 min and then concentrated in vacuo to yield 4-(piperidin-4-yloxy)pyridin-2(1H)-one hydrochloride (1.07 g, 100% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.30 (br. s., 2H) 7.64 (d, J=7.28 Hz, 1H) 6.37 (dd, J=7.28, 2.51 Hz, 1H) 6.28 (d, J=2.51 Hz, 1H) 4.57-4.96 (m, 1H) 3.11-3.36 (m, 2H) 2.85-3.11 (m, 2H) 2.00-2.29 (m, 2H) 1.64-1.98 (m, 2H). MS (ESI) 195 (M+H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f3dd8349a104bec89369069edab80c2
Source dataset
uspto-grants-2015_11
Patent number
US09174965B2

Reaction notes

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