Water → HCID 21955331, compound

HRID 2213043Notes

Reaction equation

HRID 2213043 reaction equation
[H-].[Na+].[O:3]=[C:4]1[NH:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1.Cl[CH2:21][C:22]1[N:26]([CH3:27])[N:25]=[CH:24][N:23]=1.O>CN(C)C=O>[CH3:27][N:26]1[C:22]([CH2:21][N:9]2[CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:5][C:4]2=[O:3])=[N:23][CH:24]=[N:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 736777Benzyl 3-oxopiperazine-1-carboxylateHCID 104192195-(Chloromethyl)-1-methyl-1H-1,2,4-triazole

Product 1

HCID 21955331HCID 21955331, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 281 mg, 7.0 mmol) was added to a solution of phenylmethyl 3-oxo-1-piperazinecarboxylate (1.5 g, 6.4 mmol) in dry dimethyl formamide (5 mL) and the mixture was stirred at room temperature for 30 minutes. 5-(Chloromethyl)-1-methyl-1H-1,2,4-triazole (WO0023449, 920 mg, 7.0 mmol) was added and the mixture was stirred at room temperature for 16 hours. The mixture was poured into water (150 mL) and extracted with diethyl ether (2×100 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a pale oil (2 g, 94%). m/z (ES+) 330 (M+1).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hours
  2. extractionextracted with diethyl ether (2×100 mL)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4bf7b56f941b4cf0876d668d9f6f6916
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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