Hydrochloric Acid → 1-[2-(4-Amino-1-piperidinyl)ethyl]-7-(methyloxy)-1,5-naphthyridin-2(1H)-one dihydrochloride

HRID 656896Notes

Reaction equation

HRID 656896 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:29])[N:10]2[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]2)=[N:5][CH:4]=1.[ClH:30].CO>C(Cl)(Cl)Cl.O1CCOCC1>[ClH:30].[ClH:30].[NH2:21][CH:18]1[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][N:10]2[C:11]3[C:6](=[N:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[CH:7]=[CH:8][C:9]2=[O:29])[CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 57815396tert-butyl (1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Product 1

HCID 674973941-[2-(4-Amino-1-piperidinyl)ethyl]-7-(methyloxy)-1,5-naphthyridin-2(1H)-one dihydrochloride

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl (1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-4-piperidinyl)carbamate (5.453 g, 13.565 mmol) in chloroform (30 ml) was added 4M HCl in 1,4-dioxane (30 ml) and the reaction was stirred at rt for 0.5 h before addition of MeOH (30 ml). The reaction was stirred for a further 1 h before evaporation to provide the desired compound as a slightly impure white solid (5.323 g, 105%), which was used without further purification.

Sources & evidence

ORD record
ord-bc5ef9092be94edf84c9c807a6075457
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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