Water → 4-{[bis(3-methylbutyl)amino]methyl}-N2-(3-piperidin-1-ylpropyl)benzene-1,2-diamine

HRID 2063508Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][CH:8]([CH3:38])[CH2:9][CH2:10][N:11]([CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[C:12](=O)[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([NH:22][CH2:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:14]=1.O>ClCCl>[CH3:36][CH:35]([CH3:37])[CH2:34][CH2:33][N:11]([CH2:12][C:13]1[CH:14]=[C:15]([NH:22][CH2:23][CH2:24][CH2:25][N:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[C:16]([NH2:19])=[CH:17][CH:18]=1)[CH2:10][CH2:9][CH:8]([CH3:7])[CH3:38]

Participants

Conditions

Temperature: 0 °C

Procedure

A lithium aluminium hydride solution (36 ml; 1N in THF) is added dropwise to a solution cooled down to 0° C. of N,N-bis(3-methylbutyl)-4-nitro-3-[(3-piperidin-1-ylpropyl)amino]benzamide (1.6 g). The mixture is returned to a temperature of 20° C. then heated under reflux for 6 hours and hydrolyzed with water cooled down to 0° C. followed by a 1N soda solution. After the addition of dichloromethane, the mixture is filtered on celite. After decantation of the filtrate and extractions, the combined organic phases are washed with 1N soda then with salt water, dried over Na2SO4 and concentrated under reduced pressure at 40° C. in order to produce the expected compound in the form of an oil (1.23 g, 85% yield).

Workup

customis returned to a temperature of 20° C.
temperaturethen heated
filtrationthe mixture is filtered on celite
extractionAfter decantation of the filtrate and extractions
washthe combined organic phases are washed with 1N soda
dry with materialwith salt water, dried over Na2SO4
concentrationconcentrated under reduced pressure at 40° C. in order

Sources & evidence

ORD record: ord-8682b0ccc0c44273871323feed04a11d
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288395B2

Reaction notes

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