Methanol → (S)-1-[4-(4-Amino-2-fluoro-phenyl)-piperazin-1-yl]-propan-2-ol

HRID 1262392Notes

Reaction equation

HRID 1262392 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@@H:18]([OH:20])[CH3:19])[CH2:13][CH2:12]1.CO>[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]([OH:20])[CH3:19])[CH2:13][CH2:12]2)=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 66712296(S)-1-[4-(2-Fluoro-4-nitro-phenyl)-piperazin-1-yl]-propan-2-ol

Product 1

HCID 66712180(S)-1-[4-(4-Amino-2-fluoro-phenyl)-piperazin-1-yl]-propan-2-olYield 82%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(S)-1-[4-(2-Fluoro-4-nitro-phenyl)-piperazin-1-yl]-propan-2-ol (0.583 g, 0.00206 mol) was combined with Methanol (42 mL, 1.0 mol) in a flask. The solution was passed through a 10% Pd/C CatCart (30×4 mm) in an H-cube hydrogenator at 10 bar, 30° C. for 3 hours. The reaction was concentrated and triturated with ether to yield a brown solid, (S)-1-[4-(4-Amino-2-fluoro-phenyl)-piperazin-1-yl]-propan-2-ol (425 mg, 82%). LCMS: m/z=254.09 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 6.75 (m, 1H), 6.30 (m, 2H), 4.95 (s, 2H), 4.29 (d, 1H, J=3.4 Hz), 3.77 (m, 1H), 2.81 (m, 4H), 2.22 (m, 2H), 1.04 (d, 3H, J=6.1 Hz).

Workup

  1. concentrationThe reaction was concentrated
  2. customtriturated with ether

Sources & evidence

ORD record
ord-7d6806b50cbd42ecafd2fe872250fa1a
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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