Cyanogen Bromide → 4-(4-Fluorobenzyl)-3-oxopiperazine-1-carbonitrile

HRID 1162805Notes

Reaction equation

HRID 1162805 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.[N:16]#[C:17]Br>C(Cl)Cl>[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:17]#[N:16])[CH2:9][C:8]2=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 185386381-(4-Fluorobenzyl)piperazin-2-one

Product 1

HCID 860749504-(4-Fluorobenzyl)-3-oxopiperazine-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(4-Fluorobenzyl)piperazin-2-one (0.50 g, 2.40 mmol, Example 1, Step 4) dissolved in methylene chloride (75 mL) was added diisopropylethylaime (0.84 mL, 4.80 mmol) and cyanogen bromide (0.28 g, 2.64 mmol) and the resultant solution was stirred overnight 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. The pure fractions were concentrated to yield the title compound as a white solid. 1H NMR (400 MHz, d6 DMSO) δ 7.31 (m, 2H), 7.18 (m, 2H), 4.54 (s, 2H), 3.98 (s, 2H), 3.49 (m, 2H), and 3.33 (m, 2H); ES MS (M+1)=234.3.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography on silica gel using a 0-5% MeOH/CHCl3 gradient
  3. concentrationThe pure fractions were concentrated

Sources & evidence

ORD record
ord-54f8f30e53f34c40bc0a17937081f176
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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