Ethyl 4-(2-methylpiperidin-1-yl)-3-nitrobenzoate → Ethyl 3-amino-4-(2-methylpiperidin-1-yl)benzoate

HRID 219803Notes

Reaction equation

HRID 219803 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]=1[N+:19]([O-])=O>[Pd].CO.CCOC(C)=O>[NH2:19][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:8]=1[N:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]1[CH3:1])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 1

HCID 67400209Ethyl 4-(2-methylpiperidin-1-yl)-3-nitrobenzoate

Product 1

HCID 56828460Ethyl 3-amino-4-(2-methylpiperidin-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

Ethyl 4-(2-methylpiperidin-1-yl)-3-nitrobenzoate (5 g; 17.10 mmol; 1 eq.) in a solution of MeOH/EtOAc 1:1 (340 mL, 0.05 M) was injected on a flow hydrogenation reactor (H-Cube), adapted with a Pd/C cartridge (44 mm), a flow of 1 mL/min, no heating and the full H2 option enabled, affording after evaporation of the solvents the title compound as a white solid (4.34 g, 96%). 1H NMR (DMSO-d6, 300 MHz) δ 7.34-7.33 (d, 1H), 7.21-7.18 (dd, J=8.28 Hz, 1.81 Hz, 1H), 7.06-7.03 (d, J=8.18 Hz 1H), 5.09 (br s, 2H), 4.28-4.26 (q, J=7.43 Hz, 2H), 3.11-3.07 (m, 1H), 2.97-2.88 (m, 1H), 2.47-2.3 (m, 1H), 1.83-1.65 (m, 6H), 1.32 (t, J=7.43 Hz, 3H). LC/MS (Method B): 263.2 (M+H)+. HPLC (Method A) Rt 2.60 min (Purity: 97.8%).

Workup

  1. customaffording
  2. customafter evaporation of the solvents the title compound as a white solid (4.34 g, 96%)

Sources & evidence

ORD record
ord-2e70957f0a664220955dbd4168f37f13
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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