Dimethylformamide → HCID 53741197, compound

HRID 1432913Notes

Reaction equation

HRID 1432913 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C[N:21]([CH:23]=O)C>C1COCC1.[NH4+].[Cl-].CCOC(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:1][C:2]2[CH:7]=[CH:6][C:5]([C:23]#[N:21])=[CH:4][CH:3]=2)[C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 736777Benzyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 53741197HCID 53741197, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 3-oxo-piperazine-1-carboxylic acid benzyl ester (3.0 g, 12.8 mmol) and 4-bromomethyl tolylnitrile (2.76 g, 14.1 mmol) in 135 mL of THF and 15 mL of DMF at 0° C. is added a 60% dispersion in mineral oil of NaH (0.49 g, 12.8 mmol). After 5 hours, the solution is diluted with saturated NH4Cl and EtOAc. The organic layer is washed with H2O and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography over silcia gel eluting with 20% EtOAc/CH2Cl2. The title compound is obtained as a white solid (4.01 g, 11.4 mmol). 1H NMR (CDCl3, 300 MHz) δ7.62 (d, 2H), 7.39 (m, 7H), 5.14 (s, 2H), 4.68 (s, 2H), 4.27 (s, 2H), 3.73 (m, 2H), 3.30 (m, 2H).

Workup

  1. washThe organic layer is washed with H2O and saturated NaCl
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by column chromatography over silcia gel
  6. washeluting with 20% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-77b6fb04abfe4b6f86f1af1864683a5d
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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