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

HRID 1516755Notes

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 solution of lithium aluminium hydride (36 ml; 1N in THF) is added dropwise to a solution of N,N-bis(3-methylbutyl)-4-nitro-3-[(3-piperidin-1-ylpropyl)amino]benzamide (1.6 g) cooled down to 0° C. The mixture is taken 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 taken to a temperature of 20° C.
temperaturethen heated
temperaturecooled down to 0° C.
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-39873503db8c43868b5ad79e334a96c1
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227485B2

Reaction notes

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