Potassium Carbonate → HCID 17901930, compound

HRID 403135Notes

Reaction equation

HRID 403135 reaction equation
Cl[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[NH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][NH:10][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 195092-PyridinemethanamineHCID 66052tert-Butyl chloroacetate

Product 1

HCID 17901930HCID 17901930, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-butyl 2-chloroacetate (0.83 g, 5.55 mmol) and 2-(Aminomethyl)pyridine (1.5 g, 8.32 mmol) were dissolved in 400 mL CH3CN. To this solution was added potassium carbonate (0.76 g, 5.55 mmol) and the mixture was stirred at room temperature for two days. The crude product was obtained as an oil after removal of the solvent and was purified on a silica gel preparative plate that was developed in with a 2% methanolic NH3 (7 M NH3 in methanol/98% CH2Cl2. The product was isolated as pale yellow oil (57%). 1H NMR (CDCl3) δ 8.414 (dd, 1H, Ar), 7.499 (dd, 1H, Ar), 7.200 (d, 1H, Ar), 7.013 (m, 1H, Ar), 3.806 (s, 2H, —CH2—), 3.242 (s, 2H, —CH2—), 2.458 (s, 1H, —CH—), 1.333 (s, 9H, —C(CH3)3).

Workup

  1. customThe crude product was obtained as an oil
  2. customafter removal of the solvent
  3. customwas purified on a silica gel preparative plate that

Sources & evidence

ORD record
ord-14a21595860747ab816e11624c9466e9
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

Loading…