C(OC(N1CCC([O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([N+:25]([O-:27])=[O:26])=[CH:17][N:16]=2)CC1)=O)(C)(C)C.[C:28](O)([C:30](F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[N+:25]([C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([O:14][N:16]2[CH2:30][CH2:28][CH2:23][CH2:24][CH2:15]2)=[N:16][CH:17]=1)([O-:27])=[O:26]To a cold solution of 4-(4-nitro-isoquinoline-1-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (9.68 g, 25.9 mmol, 0° C.) in DCM (100 mL) add TFA (80 mL). Stir at 22° C. for 2 hours, then remove solvent under reduced pressure. Dissolve residue in DCM and treat with 1 N sodium hydroxide to pH˜14. Isolate the aqueous phase and extract twice with DCM. Combine the organic phases and dry with anhydrous sodium sulfate. Removal of the solvent gives (4-nitro-isoquinoline-1-yloxy)-piperidine (7.06 g, 99% yield, ES+ (m/z) 274.3 [M+H]).
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