2-Pyridinecarboxaldehyde → HCID 68694406, compound

HRID 1157336Notes

Reaction equation

HRID 1157336 reaction equation
[C:1]([CH:3](P(OCC)(OCC)=O)[N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#[N:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[N:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH:41]=O>C1COCC1>[C:1]([C:3]([N:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:8][CH2:9]1)=[CH:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][N:35]=1)#[N:2]

Participants

5

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 2724254Sodium bis(trimethylsilyl)amideHCID 59511160HCID 59511160, compound

Product 1

HCID 68694406HCID 68694406, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 100 ml 3 necked round bottom flask, intermediate tert-butyl 4-(cyano(diethoxyphosphoryl)methyl)piperazine-1-carboxylate (5.5 g) was taken in dry THF (25 ml) under nitrogen. Sodium bis trimethylsilyl amide (3.3 g) was added dropwise at 0° C. and stirred for 30 min, then pyridine-2-carboxaldehyde (1.67 g) in 15 ml dry THF was added dropwise to the above reaction mixture at 0° C. Reaction mixture was stirred at room temperature for overnight. TLC was checked no starting material and the reaction mixture was quenched with saturated ammonium chloride (50 ml) and ethyl acetate was added. The organic layer was washed with brine, dried and concentrated to get crude product compound tert-butyl 4-(1-cyano-2-(pyridin-2-yl)vinyl)piperazine-1-carboxylate as yellow liquid.

Workup

  1. customReaction mixture
  2. stirringwas stirred at room temperature for overnight
  3. customthe reaction mixture was quenched with saturated ammonium chloride (50 ml) and ethyl acetate
  4. additionwas added
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-82dace5f1455435584a9e1e4f2b6fa2a
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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