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

HRID 1435406Notes

Reaction equation

HRID 1435406 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:18][C:19](=[O:21])[CH3:20])[CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)([O-])=O>CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:18][C:19](=[O:21])[CH3:20])[CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

4

Reactant 1

HCID 57937362N-{3-Nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamide

Product 1

HCID 57937312N-{3-Amino-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolvent

Procedure

N-{3-Nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamide (28.9 g, 98.5 mmol) was dissolved in 1.0 L of EtOAc containing a catalytic amount of 10% Pd/C. The solution was shaken under H2 atmosphere (40 psi) using a Parr hydrogenation apparatus overnight at room temperature. The solution was filtered through celite and the solvent was evaporated. Yield: 25.9 g (99%). 1H NMR (400 MHz, CHLOROFORM-D) δ 1.4 (m, 2 H), 1.7 (m, 2 H), 1.82-1.91 (m, 1 H), 2.13 (s, 3 H), 2.99 (d, J=6.64, 2 H), 3.42 (dt, J=11.86, 2.05 Hz, 2 H), 4.02 (dd, J=10.94, 3.71 Hz, 2 H), 6.84 (d, J=9.37 Hz, 1 H), 7.20 (br.s, 1 H), 7.81 (dd, J=9.37, 2.54 Hz, 1 H), 8.09 (d, J=2.54 Hz, 1 H), 8.10-8.12 (m, 1 H).

Workup

  1. customa Parr hydrogenation apparatus overnight
  2. customat room temperature
  3. filtrationThe solution was filtered through celite
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-66f672d8409c402bb1ae0dc5c446665e
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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