Water → HCID 54059542, compound

HRID 1357762Notes

Reaction equation

HRID 1357762 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.[C:24]1([C:30]2([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][CH2:38][CH2:39][NH2:40])[CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>C1COCC1>[C:24]1([C:30]2([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:31][CH2:32][N:33]([CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:9](=[O:11])[CH:8]=[CH:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH2:34][CH2:35]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 1019843-(3-Pyridinyl)-2-propenoic acidHCID 230041441-(4-Aminobutyl)-4,4-diphenylpiperidine

Product 1

HCID 54059542HCID 54059542, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.4 g (16.0 mmol) 3-(3-pyridyl)-acrylic acid and 2.9 g (17.6 mmol) CDI are heated under reflux in 150 ml absolute THF under moisture exclusion. After an hour, this is cooled to RT and 6.0 g (19.2 mmol) 4-(4,4-diphenyl-piperidin-1-yl)-butylamine, dissolved in 25 ml absolute THF, are added dropwise. After addition, this is stirred for a further three hours at RT and left to stand overnight. The mixture is poured into 200 ml water and extracted three times each with 100 ml 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 pre-purified over silica gel with CHCl3/CH3OH (95/5). After removal of the solvent, crystallization occurs from 130 ml isopropanol: Colorless crystals with MP. 207-208° C.: Yield 2.0 g (28%).

Workup

  1. waitAfter an hour
  2. additionare added dropwise
  3. additionAfter addition
  4. waitleft
  5. waitto stand overnight
  6. extractionextracted three times each with 100 ml acetic acid ethyl ester
  7. stirringby shaking
  8. washThe combined organic phases are washed with saturated NaCl-solution
  9. dry with materialdried over sodium sulfate
  10. customthe solvent is removed under vacuum
  11. customThe residue is chromatographically pre-purified over silica gel with CHCl3/CH3OH (95/5)
  12. customAfter removal of the solvent, crystallization
  13. customwith MP. 207-208° C.

Sources & evidence

ORD record
ord-ddbfeb8890c049dc903ff753e48af703
Source dataset
uspto-grants-2003_07
Patent number
US06593344B1

Reaction notes

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