Methyl-(1-methyl-piperidin-4-yl)-(5-nitro-benzooxazol-2-yl)-amine → N2-Methyl-N2-(1-methyl-piperidin-4-yl)-benzooxazole-2,5-diamine

HRID 601548Notes

Reaction equation

[CH3:1][N:2]([CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:6]=2[N:7]=1>C(O)(=O)C.[Fe]>[CH3:1][N:2]([CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:6]=2[N:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Dissolve methyl-(1-methyl-piperidin-4-yl)-(5-nitro-benzooxazol-2-yl)-amine (0.583 g, 2.01 mmol), in acetic acid (8 mL), and add iron (1.12 g, 20.1 mmol) to the solution. Stir the mixture at 40° C. for 3 h. Filter the reaction mixture through Celite® and wash with water/MeOH. Concentrate the reaction mixture in vacuo. Subject the residue to silica gel flash column chromatography, eluting with 10% 2N NH3 in MeOH/CH2Cl2, to yield the desired product (0.474 g, 91%). MS (ES+) 261.2 (M+1)+.

Workup

filtrationFilter the reaction mixture through Celite®
washwash with water/MeOH
concentrationConcentrate the reaction mixture in vacuo
washeluting with 10% 2N NH3 in MeOH/CH2Cl2

Sources & evidence

ORD record: ord-2e3af89be4e94b01a99979ff2ef8e569
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902356B2

Reaction notes

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