Potassium Cyanide → Benzyl 4-(4-(cyanomethyl)pyridin-2-yl)piperazine-1-carboxylate

HRID 517561Notes

Reaction equation

HRID 517561 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:11][CH2:10]2)[CH:4]=1.[C-:25]#[N:26].[K+]>CS(C)=O.C([O-])(O)=O.[Na+]>[C:25]([CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:11][CH2:10]2)[CH:4]=1)#[N:26]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 86711500Benzyl 4-(4-(chloromethyl)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 86711501Benzyl 4-(4-(cyanomethyl)pyridin-2-yl)piperazine-1-carboxylateYield 51.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of benzyl 4-(4-(chloromethyl)pyridin-2-yl)piperazine-1-carboxylate (5.0 g, 14.5 mmol) and KCN (2.8 g, 43.5 mmol) in DMSO (30 mL) was stirred at RT overnight, and then diluted with sat. NaHCO3 (300 mL) and extracted with EtOAc (3×200 mL). The combined organic layers were washed with H2O (50 mL) and brine (20 mL), dried over Na2SO4, filtered and concentrated to afford crude product, which was purified by silica gel column chromatography (Petroleum ether:EtOAc=1:1) to give benzyl 4-(4-(cyanomethyl)pyridin-2-yl)piperazine-1-carboxylate as a yellow solid (2.5 g, 51%). MS (ES+) C19H20N4O2 requires: 336, found: 337[M+H]+.

Workup

  1. extractionextracted with EtOAc (3×200 mL)
  2. washThe combined organic layers were washed with H2O (50 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford crude product, which
  7. customwas purified by silica gel column chromatography (Petroleum ether:EtOAc=1:1)

Sources & evidence

ORD record
ord-06b3fb34ff284446b8674ebf8ba1fad3
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

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