N-Methyl-N-(4-nitro-3-piperidin-1-yl-phenyl)-acetamide → n-(4-Amino-3-piperidin-1-yl-phenyl)-n-methyl-acetamide

HRID 32912Notes

Reaction equation

HRID 32912 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:7]=1)[C:3](=[O:5])[CH3:4]>[Pd]>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([N:2]([CH3:1])[C:3](=[O:5])[CH3:4])=[CH:7][C:8]=1[N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

3

Reactant 1

HCID 69310207N-Methyl-N-(4-nitro-3-piperidin-1-yl-phenyl)-acetamide

Product 1

HCID 69310230n-(4-Amino-3-piperidin-1-yl-phenyl)-n-methyl-acetamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Using a procedure similar to Example 3, step (c), N-methyl-N-(4-nitro-3-piperidin-1-yl-phenyl)-acetamide (67 mg, 0.24 mmol, as prepared in the previous step) was stirred with 5% Pd—C (45 mg) under H2 to afford N-(4-amino-3-piperidin-1-yl-phenyl)-N-methyl-acetamide which was used immediately. Using a procedure similar to Example 3, step (d) this was coupled to 5-cyano-furan-2-carbonyl chloride (52 mg, 0.33 mmol) in the presence of DIEA (107 μL, 0.55 mmol) to afford 7.3 mg (8%) of the title compound as a waxy solid. 1H-NMR (CDCl3; 400 MHz): δ 9.66 (s, 1H), 8.48 (d, 1H, J=9.2 Hz), 7.34 (d, 1H, J=3.7 Hz), 7.26 (d, 1H, J=3.3 Hz), 7.03-7.01 (m, 2H), 3.27 (s, 3H,), 2.88-2.86 (m, 4H), 1.90 (s, 3H), 1.88-1.82 (m, 4H), 1.63 (br s, 2H); Mass spectrum (ESI, m/z): Calcd. for C20H22N4O3, 367.1 (M+1), found 367.2.

Workup

  1. customas prepared in the previous step)

Sources & evidence

ORD record
ord-e540394435d44875a3b56d9da825bd3c
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Reaction notes

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