Water → HCID 54184207, compound

HRID 2251919Notes

Reaction equation

HRID 2251919 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.C1N=CN(C(N2C=NC=C2)=O)C=1.[OH:24][C:25]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH2:33].O>C1COCC1>[OH:24][C:25]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:9](=[O:11])[CH:8]=[CH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 1019843-(3-Pyridinyl)-2-propenoic acidHCID 17940768HCID 17940768, compound

Product 1

HCID 54184207HCID 54184207, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.4 g (23.0 mmol) 3-(3-pyridyl)-acrylic acid and 3.7 g (23.0 mmol) CDI are heated under reflux in 50 ml THF under moisture exclusion. After one hour this is cooled to RT and 6.5 g (21.9 μmmol) 8-hydroxy-8,8-diphenyloctylamine, dissolved in 20 ml THF, is added dropwise. After complete addition, stirring is carried out for a further three hours at RT and this is left to stand overnight. 50 ml water is added to the mixture and extracted three times with acetic acid ethyl ester by shaking. The combined organic phases are washed with saturated NaCl solution, dried over sodium sulfate, and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CHCl3/CH3OH (95/5) and subsequently, crystallized twice from 200-ml and 140 ml acetic acid ethyl ester: Colorless crystals with MP. 139-140° C. in a yield of 3.7 g (39%). C28H32N2O2 (428.6)

Workup

  1. additionis added dropwise
  2. additionAfter complete addition
  3. waitthis is left
  4. waitto stand overnight
  5. extractionextracted three times with acetic acid ethyl ester
  6. stirringby shaking
  7. washThe combined organic phases are washed with saturated NaCl solution
  8. dry with materialdried over sodium sulfate
  9. customthe solvent is removed under vacuum
  10. customThe residue is chromatographically purified over silica gel with CHCl3/CH3OH (95/5)
  11. customsubsequently, crystallized twice from 200-ml and 140 ml acetic acid ethyl ester
  12. customwith MP. 139-140° C.

Sources & evidence

ORD record
ord-fac65630a5f34495a61be635ef7e5e67
Source dataset
uspto-grants-2008_01
Patent number
US07320993B1

Reaction notes

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