Trifluoroacetic acid → 4-(N-((4-Nitrobenzyl)oxycarbonyl)-N-(prop-1-yl)amino)-piperidine trifluoroacetate

HRID 2185552Notes

Reaction equation

HRID 2185552 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6]1)[CH2:2][CH3:3].[N+:18]([C:21]1[CH:31]=[CH:30][C:24]([CH2:25][O:26][C:27](Cl)=[O:28])=[CH:23][CH:22]=1)([O-:20])=[O:19].[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33]>C(Cl)Cl>[F:35][C:34]([F:37])([F:36])[C:32]([OH:38])=[O:33].[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([CH2:25][O:26][C:27]([N:4]([CH:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)[CH2:1][CH2:2][CH3:3])=[O:28])=[CH:30][CH:31]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 782054-Nitrobenzyl chloroformateHCID 22458258Tert-butyl 4-(propylamino)piperidine-1-carboxylate

Product 1

HCID 224582504-(N-((4-Nitrobenzyl)oxycarbonyl)-N-(prop-1-yl)amino)-piperidine trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by the reaction of 4-(N-(prop-1-yl)amino)-1-tert-butoxycarbonylpiperidine (from Example 17, Step A) with (4-nitrobenzyl)chloroformate, followed by treatment of the product with 50% TFA in CH2Cl2 to remove the tert-butoxycarbonyl group, affording the title compound. ESI-MS: 322.2 (M+H).

Workup

  1. customto remove the tert-butoxycarbonyl group

Sources & evidence

ORD record
ord-bf50bf7bc7754f3ebba738292e7113fe
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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