N-(1-benzyl-piperidin-4-yl)-2-methoxy-6-nitrobenzamide → (2-Amino-6-methoxy-benzyl)-(1-benzyl-piperidin-4-yl)-amine

HRID 1353605Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=O)[C:16]2[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[CH:18][C:17]=2[O:25][CH3:26])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCOCC1>[NH2:22][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([O:25][CH3:26])[C:16]=1[CH2:15][NH:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1

Participants

Conditions

Temperature: 0 °C

Procedure

Into a flame dried flask, N-(1-benzyl-piperidin-4-yl)-2-methoxy-6-nitrobenzamide (1.0 g, 2.8 mmol) and lithium aluminium hydride (0.31 g, 8.45 mmol) were combined. To the mixture was added anhydrous 1,4-dioxane (15 mL). The mixture was slowly brought to reflux over 1 h and stirred at reflux for 16 h. The reaction mixture was cooled to 0° C. and excess lithium aluminium hydride destroyed by dropwise addition of methanol, followed by careful addition of 20% potassium hydroxide. The aluminum salts were filtered, the filtrate concentrated and used as is for the next reaction.

Workup

customInto a flame dried flask
temperatureto reflux over 1 h
temperatureat reflux for 16 h
customexcess lithium aluminium hydride destroyed by dropwise addition of methanol
additionfollowed by careful addition of 20% potassium hydroxide
filtrationThe aluminum salts were filtered
concentrationthe filtrate concentrated
customas is for the next reaction

Sources & evidence

ORD record: ord-2e52f3590e1748abbb54c8462b220469
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220862B2

Reaction notes

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