HCID 67519506, compound → N4-(tetrahydro-2H-pyran-4-ylmethyl)quinoline-3,4-diamine

HRID 1925472Notes

Reaction equation

HRID 1925472 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>[Pd].C(O)C>[O:19]1[CH2:18][CH2:17][CH:16]([CH2:15][NH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]=[CH:5][C:4]=2[NH2:1])[CH2:21][CH2:20]1

Participants

4

Reactant 1

HCID 67519506HCID 67519506, compound

Product 1

HCID 69001829N4-(tetrahydro-2H-pyran-4-ylmethyl)quinoline-3,4-diamineYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-nitro-N-(tetrahydro-2H-pyran-4-ylmethyl)quinolin-4-amine (2.50 g), 10% palladium on carbon (0.25 g), and ethanol (40 mL) was placed under hydrogen pressure on a Parr apparatus. When the reaction was complete, the mixture was filtered through a layer of CELITE filter agent. The filter cake was washed with ethanol. The filtrate was concentrated under reduced pressure to provide 2.23 g of N4-(tetrahydro-2H-pyran-4-ylmethyl)quinoline-3,4-diamine as a yellowish-orange oil.

Workup

  1. filtrationthe mixture was filtered through a layer of CELITE filter agent
  2. washThe filter cake was washed with ethanol
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-397a1a3d5e6143559a390f1ee6007b86
Source dataset
uspto-grants-2012_05
Patent number
US08178677B2

Reaction notes

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