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

HRID 1262391Notes

Reaction equation

HRID 1262391 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.CO.[CH2:19]1[O:22][C@H:20]1[CH3:21]>>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:19][C@@H:20]([OH:22])[CH3:21])[CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 887MethanolHCID 146262(2S)-2-MethyloxiraneHCID 27830661-(2-fluoro-4-nitrophenyl)piperazine

Product 1

HCID 66712296(S)-1-[4-(2-Fluoro-4-nitro-phenyl)-piperazin-1-yl]-propan-2-olYield 93%

Procedure

1-(2-Fluoro-4-nitro-phenyl)-piperazine (0.500 g, 0.00222 mol) was dissolved in Methanol (11.0 mL, 0.272 mol) and the reaction mixture was placed in a sealed tube. (S)-(−)-Propylene Oxide (0.235 mL, 0.00335 mol) was then added at room temperature and the reaction was stirred for 19 hours. The reaction was concentrated to yield a yellow solid, (S)-1-[4-(2-Fluoro-4-nitro-phenyl)-piperazin-1-yl]-propan-2-ol (583 mg, 93%). LCMS: m/z=284.10 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 8.00 (d, 2H, J=11.3 Hz), 7.16 (m, 1H), 4.36 (d, 1H, J=4.0 Hz), 3.80 (m, 1H), 3.28 (m, 4H), 2.57 (m, 4H), 2.26 (m, 2H), 1.06 (d, 3H, J=6.2 Hz).

Workup

  1. customthe reaction mixture was placed in a sealed tube
  2. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-b8ec69b325fe4188a9d2b6a71137b278
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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