Methanol → 2-[4-(4-Amino-2-fluoro-phenyl)-piperazin-1-yl]-acetamide

HRID 1262388Notes

Reaction equation

HRID 1262388 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]([NH2:20])=[O:19])[CH2:13][CH2:12]1.CO.CN(C)C=O>[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([NH2:20])=[O:19])[CH2:13][CH2:12]2)=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6228DimethylformamideHCID 471845052-[4-(2-Fluoro-4-nitro-phenyl)-piperazin-1-yl]-acetamide

Product 1

HCID 667125502-[4-(4-Amino-2-fluoro-phenyl)-piperazin-1-yl]-acetamideYield 97.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2-[4-(2-Fluoro-4-nitro-phenyl)-piperazin-1-yl]-acetamide (0.558 g, 0.00198 mol) was combined with Methanol (60 mL, 1 mol) and N,N-Dimethylformamide (10 mL, 0.1 mol). The solution was passed through a 10% Pd/C CatCart (55×4 mm) in an H-cube hydrogenator at 10 bar, 30° C. for 3.5 hours. The reaction was concentrated to yield a yellow solid, 2-[4-(4-Amino-2-fluoro-phenyl)-piperazin-1-yl]-acetamide (485 mg, 97%). LCMS: m/z=253.06 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 7.14 (d, 2H), 6.76 (m, 1H), 6.31 (m, 2H), 4.97 (br s, 2H), 2.87 (m, 6H), 2.52 (m, 4H).

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-53176327ee7e4aacbc5f0d6bc70d9420
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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