N-(2-Aminoethyl)piperidine → N,N-diethyl-3-nitro-4-{[2-(1-piperidinyl)ethyl]amino}benzamide

HRID 1796461Notes

Reaction equation

[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](F)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2].[N:18]1([CH2:24][CH2:25][NH2:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>CCO.Cl>[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([NH:26][CH2:25][CH2:24][N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

Following general procedure 2B: A mixture of N,N-diethyl-4-fluoro-3-nitrobenzamide (1.0 g, 4.2 mmol), 2-(1-piperidinyl)ethanamine (0.564 mL, 3.96 mmol) in 80% aq. EtOH (30 mL) was heated at 85° C. for 10 hours. After the usual work-up, the crude mixture was dissolved in 1 N HCl (40 mL) and washed with CH2Cl2 (2×10 mL). The aqueous layer was basified with 5 N NaOH (10 mL) and extracted with CH2Cl2 (3×10 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo to provide the title compound (0.800 g, 57%) as a bright yellow solid which was used without further purification. 1H-NMR (CDCl3): δ 8.64 (br s, 1H), 8.25 (d, J=2.4 Hz, 1H), 7.53 (d, J=8.8 Hz, 1H), 6.82 (d, J=8.8 Hz, 1H), 3.41 (br s, 4H), 3.35 (br s, 2H), 2.64 (br s, 2H), 2.53 (br s, 4H), 1.61 (br s, 4H), 1.44 (br s, 2H), 1.19 (t, J=7.0 Hz, 6H).

Workup

washwashed with CH2Cl2 (2×10 mL)
extractionextracted with CH2Cl2 (3×10 mL)
dry with materialThe combined organic phases were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-717bc7cc722d447983bb779143ff17e7
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030139B2

Reaction notes

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