Methyl Isocyanate → 4-(4-Fluorobenzyl)-N-methyl-3-oxopiperazine-1-carboxamide

HRID 1162803Notes

Reaction equation

HRID 1162803 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][CH2:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[CH3:16][N:17]=[C:18]=[O:19]>C1COCC1>[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:18]([NH:17][CH3:16])=[O:19])[CH2:9][C:8]2=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 185386381-(4-Fluorobenzyl)piperazin-2-one

Product 1

HCID 684315454-(4-Fluorobenzyl)-N-methyl-3-oxopiperazine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Fluorobenzyl)piperazin-2-one (0.40 g, 1.9 mmol, Example 1, Step 4) was dissolved in anhydrous THF (20 mL) under nitrogen and methyl isocyanate (0.96 mL, 1.9 mmol, 2M solution in THF) was added. The reaction was allowed to stir for two hours at room temperature. The solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel using a 0-5% MeOH/CHCl3 gradient elution. Collection and concentration of the appropriate fractions provided the title compound as a white solid. 1H NMR (400 MHz, d6 DMSO) δ 7.29 (m, 2H), 7.16 (m, 2H), 6.55 (d, 1H, J=4.2 Hz), 4.51 (s, 2H), 3.97 (s, 2H), 3.50 (t, 2H, J=5.4 Hz), 3.22 (t, 2H, J=5.4 Hz), and 2.56 (d, 3H, J=4.4 Hz); ES MS (M+1)=266.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography on silica gel using
  3. washa 0-5% MeOH/CHCl3 gradient elution
  4. customCollection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-749e6d24f55e43deb1e31dfa6a2765ae
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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