N-methyl-N-{3-nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamide → N-{3-Amino-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}-N-methylacetamide

HRID 1987203Notes

Reaction equation

HRID 1987203 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[C:8]([N+:20]([O-])=O)[CH:7]=1)[C:3](=[O:5])[CH3:4]>C(OCC)(=O)C.[Pd]>[NH2:20][C:8]1[CH:7]=[C:6]([N:2]([CH3:1])[C:3](=[O:5])[CH3:4])[CH:11]=[CH:10][C:9]=1[NH:12][CH2:13][CH:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1

Participants

4

Reactant 1

HCID 57441081N-methyl-N-{3-nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamide

Product 1

HCID 57441082N-{3-Amino-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}-N-methylacetamideYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-Methyl-N-{3-nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamide (21.7 g, 70.5 mmol) was hydrogenated in ethyl acetate (500 mL) catalyzed by 10% Pd/C (1.0 g) at 30-40 psi H2 in Parr shaker for 18 h at room temperature. After filtration through celite and concentration, 19.6 g (100%) of a purple solid was obtained. 1H NMR (400 MHz, CHLOROFORM-D): δ 1.35-1.50 (m, 2 H), 1.67 (s, 1 H), 1.73-1.81 (m, 2 H), 1.88 (s, 3 H), 1.88-1.99 (m, 1 H), 3.04 (d, J=6.64 Hz, 2 H), 3.20 (s, 3 H), 3.33-3.48 (m, 4 H), 3.97-4.08 (m, 2 H), 6.54 (d, J=1.76 Hz, 1 H), 6.60-6.63 (m, 2 H); MS (ESI) (M+H)+: 278.7

Workup

  1. filtrationAfter filtration
  2. concentrationthrough celite and concentration

Sources & evidence

ORD record
ord-69c1765c036c4010838b3d4c37ed0e65
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Reaction notes

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