4-Piperidineethanol → HCID 10389386, compound

HRID 2079563Notes

Reaction equation

HRID 2079563 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3[N:14]=[C:15]([CH3:19])[N:16]=[C:17](Cl)[C:12]=3[C:11]([CH3:20])=[CH:10]2)=[C:4]([CH3:21])[CH:3]=1.[OH:22][CH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3[N:14]=[C:15]([CH3:19])[N:16]=[C:17]([N:28]4[CH2:29][CH2:30][CH:25]([CH2:24][CH2:23][OH:22])[CH2:26][CH2:27]4)[C:12]=3[C:11]([CH3:20])=[CH:10]2)=[C:4]([CH3:21])[CH:3]=1

Participants

6

Reactant 4

HCID 739534-PiperidineethanolHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 60035463HCID 60035463, compound

Product 1

HCID 10389386HCID 10389386, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-(4-bromo-2,6-dimethylphenyl)-4-chloro-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidine (6.0 g), 4-(2-hydroxyethyl)piperidine (3.2 g), N,N-diisopropylethylamine (3.2 g) in ethanol (15 mL) was heated at reflux for 5.5 hours. The reaction mixture was cooled to room temperature, poured into a saturated aqueous sodium hydrogencarbonate, and then extracted with ethyl acetate three times. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=2:1) to obtain 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-ethanol as a white solid (6.41 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5.5 hours
  3. extractionextracted with ethyl acetate three times
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. custompurified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-3e0dfaa99b104971ad78697c45fb21fe
Source dataset
uspto-grants-2011_04
Patent number
US07932259B2

Reaction notes

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