Tert-butyl 4-hydroxy-4-{[(3-nitroquinolin-4-yl)amino]methyl}piperidine-1-carboxylate → Tert-butyl 4-{[(3-aminoquinolin-4-yl)amino]methyl}-4-hydroxypiperidine-1-carboxylate

HRID 44698Notes

Reaction equation

HRID 44698 reaction equation
[OH:1][C:2]1([CH2:15][NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[CH:19][C:18]=2[N+:27]([O-])=O)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1>[Pt].C(O)C>[NH2:27][C:18]1[CH:19]=[N:20][C:21]2[C:26]([C:17]=1[NH:16][CH2:15][C:2]1([OH:1])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:4][CH2:3]1)=[CH:25][CH:24]=[CH:23][CH:22]=2

Participants

4

Reactant 1

HCID 57515384Tert-butyl 4-hydroxy-4-{[(3-nitroquinolin-4-yl)amino]methyl}piperidine-1-carboxylate

Product 1

HCID 57515385Tert-butyl 4-{[(3-aminoquinolin-4-yl)amino]methyl}-4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

The starting material tert-butyl 4-hydroxy-4-{[(3-nitroquinolin-4-yl)amino]methyl}piperidine-1-carboxylate (20.23 g, 50.3 mmol) was divided into two portions. To each portion was added ethanol (220 mL) and 5% platinum on carbon (1.1 g). Both portions were hydrogenated on a Parr apparatus at 40 psi (2.8×105 Pa) overnight. The mixtures were filtered through CELITE filter agent. The filtrates were combined and concentrated to provide the product tert-butyl 4-{[(3-aminoquinolin-4-yl)amino]methyl}-4-hydroxypiperidine-1-carboxylate as a brown oil. The product was concentrated twice from toluene and once from chloroform and used in the subsequent experiment.

Workup

  1. customwere hydrogenated on a Parr apparatus at 40 psi (2.8×105 Pa) overnight
  2. filtrationThe mixtures were filtered through CELITE
  3. filtrationfilter agent
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-99e80450dce24c41bbe49300204693cc
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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