Benzaldehyde → HCID 68691357, compound

HRID 1157320Notes

Reaction equation

HRID 1157320 reaction equation
[H-].[Na+].[C:3]([CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)#[N:4].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[C:3]([C:5]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)#[N:4]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 24758Sodium hydrideHCID 21936030Tert-butyl 4-(cyanomethyl)piperazine-1-carboxylate

Product 1

HCID 68691357HCID 68691357, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To sodium hydride (0.1 g) taken in dry DMF (5 ml), under nitrogen, compound tert-butyl 4-(cyanomethyl)piperazine-1-carboxylate (0.5 g) was added and allowed to stir at room temperature for half an hour. Benzaldehyde (280 mg) was added to the above reaction mixture and allowed to stir for 3 hours at room temperature. The reaction mixture was quenched with ice water (50 ml) and extracted with ethyl acetate (3×10 ml). The combined organic layer was washed with brine (10 ml), dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography using MeOH: CH2Cl2 (0.5:9.5) as an eluent to afford tert-butyl 4-(1-cyano-2-phenylvinyl)piperazine-1-carboxylate as pure product.

Workup

  1. stirringto stir for 3 hours at room temperature
  2. customThe reaction mixture was quenched with ice water (50 ml)
  3. extractionextracted with ethyl acetate (3×10 ml)
  4. washThe combined organic layer was washed with brine (10 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-b0907b4d64b446efbd0194792cf4edbf
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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