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

HRID 656871Notes

Reaction equation

HRID 656871 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:28])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([NH:20]C(=O)OC(C)(C)C)[CH2:16][CH2:15]2)=[N:4][CH:3]=1.[ClH:29]>C(Cl)(Cl)Cl.CO.O1CCOCC1>[ClH:29].[ClH:29].[NH2:20][CH:17]1[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][N:9]2[C:10]3[C:5](=[N:4][CH:3]=[C:2]([F:1])[CH:11]=3)[CH:6]=[CH:7][C:8]2=[O:28])[CH2:19][CH2:18]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 57815181tert-butyl (1-(2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Product 1

HCID 674992211-[2-(4-Amino-1-piperidinyl)ethyl]-7-fluoro-1,5-naphthyridin-2(1H)-one Dihydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1,1-dimethylethyl {1-[2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl]-4-piperidinyl}carbamate (1.591 g, 4.079 mmol) in chloroform (15 ml) and MeOH (15 ml) was added 4M HCl in 1,4-dioxane (15 ml). The reaction was stirred at rt for 0.5 h before evaporation to provide the desired compound as a slightly impure white solid which was used without further purification (1.633 g, 110%).

Sources & evidence

ORD record
ord-fadced28725e4f08a954489f35126434
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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