Ethyl chloroformate → HCID 54409106, compound

HRID 1294461Notes

Reaction equation

HRID 1294461 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]([OH:11])=O)[CH:2]=1.C(OC(Cl)=O)C.[CH2:18]([N:25]1[CH2:30][CH2:29][CH:28]([O:31][CH2:32][CH2:33][CH2:34][NH2:35])[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[CH2:18]([N:25]1[CH2:26][CH2:27][CH:28]([O:31][CH2:32][CH2:33][CH2:34][NH:35][C:9](=[O:11])[CH:8]=[CH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:29][CH2:30]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 1019843-(3-Pyridinyl)-2-propenoic acidHCID 18425738200868-41-3

Product 1

HCID 54409106HCID 54409106, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

2.4 g (16.2 mmol) 3-(3-pyridyl)-acrylic acid and 2.3 ml (16.2 mmol) TEA are suspended in 50 ml abs. toluene and a solution of 1.5 ml (15.5 mmol) chloroformic acid ethyl ester in 20 ml abs. toluene are added dropwise under moisture exclusion and light cooling. This yellow suspension is stirred at RT for two hours and then a solution of 3.5 g (14.1 mmol) 3-(1-benzylpiperidin-4-yloxy)-propylamine in 20 ml abs. toluene is added dropwise. The mixture is stirred for two hours at RT and extracted by shaking three times in the heat, each with 10 ml water, 2 M sodium hydroxide and water again. The organic phase is concentrated under vacuum and the orange colored oily residue is chromatographically purified twice over silica gel with CHCl3/CH3OH/NH4OH (90/9/1 and 95/5/0 to 90/10/0) and crystallized from 10 ml acetic acid ethyl ester. Colorless crystals remain with a MP of 100–102° C.; yield: 1.9 g (35%).

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred for two hours at RT
  3. extractionextracted
  4. stirringby shaking three times in the heat
  5. concentrationThe organic phase is concentrated under vacuum
  6. customthe orange colored oily residue is chromatographically purified twice over silica gel with CHCl3/CH3OH/NH4OH (90/9/1 and 95/5/0 to 90/10/0)
  7. customcrystallized from 10 ml acetic acid ethyl ester

Sources & evidence

ORD record
ord-8a3e165dc49443b7b6ec26c5b54c6fe3
Source dataset
uspto-grants-2007_07
Patent number
US07241745B2

Reaction notes

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