4-(4-Methyl-1,4-diazepan-1-yl)-2-(propan-2-yloxy)nitrobenzene → 2-Isopropoxy-4-(4-methyl-1,4-diazepan-1-YL)aniline

HRID 518881Notes

Reaction equation

HRID 518881 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([O:18][CH:19]([CH3:21])[CH3:20])[CH:10]=2)[CH2:4][CH2:3]1>CO.[Pd]>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([O:18][CH:19]([CH3:21])[CH3:20])[CH:10]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 866980294-(4-Methyl-1,4-diazepan-1-yl)-2-(propan-2-yloxy)nitrobenzene

Product 1

HCID 830025762-Isopropoxy-4-(4-methyl-1,4-diazepan-1-YL)anilineYield 91.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 267 mg of 4-(4-methyl-1,4-diazepan-1-yl)-2-(propan-2-yloxy)nitrobenzene in 90 ml of methanol is hydrogenated using an H-cube, on a cartridge of 10% palladium-on-carbon, at a flow rate of 1 ml/min. The hydrogenated solution is concentrated under reduced pressure, so as to obtain 220 mg of 4-(4-methyl-1,4-diazepan-1-yl)-2-(propan-2-yloxy)aniline in the form of a grey oil.

Workup

  1. concentrationThe hydrogenated solution is concentrated under reduced pressure

Sources & evidence

ORD record
ord-e61f98b05fc1411194c0dd21cdb0d1d6
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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