Ethyl chloroformate → HCID 54409106, compound

HRID 1280770Notes

Reaction equation

HRID 1280770 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>>[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

4

Reactant 3

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

Product 1

HCID 54409106HCID 54409106, compound

Procedure

2.4 g (16.2 mmol) 3-(3-pyridyl)-acrylic acid and 2.3 g (16.2 mmol) TEA were suspended in 50 ml abs. tolueneand a solution of 1.5 ml (15.5 mmol) chloroformic ethyl ester in 20 ml abs. tolueneis added dropwise under moisture exclusion and gentle cooling. This yellow suspension is stirred two hours at RT and then a solution of 3.5 g (14.1 mmol) 3-(1-benzylpiperidine-4-yloxy)-propylamine in 20 ml abs. tolueneis added dropwise. The mixture is stirred at RT and subsequently extracted by shaking in the heat three times with 10 ml water, 2M sodium hydroxide solution and again with water, respectively. 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 twice from 10 ml acetic acid ethyl ester. Colorless crystals with a MP of 100-102° C. were recovered; yield: 1.9 g (35%).

Workup

  1. additiontolueneis added dropwise under moisture exclusion and gentle cooling
  2. additiontolueneis added dropwise
  3. stirringThe mixture is stirred at RT
  4. extractionsubsequently extracted
  5. stirringby shaking in the
  6. temperatureheat three times with 10 ml water, 2M sodium hydroxide solution
  7. concentrationThe organic phase is concentrated under vacuum
  8. 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)
  9. customcrystallized twice from 10 ml acetic acid ethyl ester
  10. customColorless crystals with a MP of 100-102° C. were recovered

Sources & evidence

ORD record
ord-9f23618fda4b43ebaaaa4587bb116614
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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