Triethylamine → HCID 10823223, compound

HRID 321937Notes

Reaction equation

HRID 321937 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.CCN(CC)CC.[C:16]1([O:22][C:23](Cl)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl.CCOC(C)=O>[O:22]([C:23]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 773174-Pyridinemethanamine

Product 1

HCID 10823223HCID 10823223, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(aminomethyl)pyridine (10.7 g, 98.5 mmol) in CH2Cl2 (245 mL) at 0°, was added Et3N (14.2 mL, 19.9 g, 197 mmol) followed by dropwise addition of phenylchloroformate (14.8 mL, 18.5 g, 118 mmol). After stirring for 1 h, the resulting mixture was diluted with EtOAc (1.5 L), the organic phase was washed twice with water and brine, dried over sodium sulfate and concentrated under vacuum. Chromatography (SiO2, gradient EtOAc to 10% MeOH/CHCl3) gave a yellow solid which was recrystallized from EtOAc:hexane (2:1), to yield the desired compound (9.55 g, 41.85 mmol, 42% yield).

Workup

  1. washthe organic phase was washed twice with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customChromatography (SiO2, gradient EtOAc to 10% MeOH/CHCl3) gave a yellow solid which
  5. customwas recrystallized from EtOAc:hexane (2:1)

Sources & evidence

ORD record
ord-25196ab5f37b4daca1bb8e6f390330ca
Source dataset
uspto-grants-2001_04
Patent number
US06211170B1

Reaction notes

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