Water → HCID 58626121, compound

HRID 1161674Notes

Reaction equation

HRID 1161674 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[OH:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.O>C(O)CCC>[Cl:8][C:6]1[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=[C:2]([N:19]2[CH2:20][CH2:21][CH:16]([OH:15])[CH2:17][CH2:18]2)[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 77338FenclorimHCID 79341Piperidin-4-ol

Product 1

HCID 58626121HCID 58626121, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 4,6-dichloro-2-phenyl pyrimidine (1 g. 4.42 mmol) and triethyl mol amine (1.78 g, 17.6 mmol) in n-butanol (10 mL) was added 4-hydroxy piperidine (0.44 g, 4.4 mmol) to temperature in the range of 20-40° C. with stirring. The mixture was then stirred under reflux for 16 hours under nitrogen. The mixture was cooled to room temperature, poured into water (25 mL) and extracted with EtOAc (2×15 mL). Organic layers were collected, combined dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography using EtOAc-pet ether to give the desired compound (1.15 g, 91% yield).

Workup

  1. stirringThe mixture was then stirred
  2. temperatureunder reflux for 16 hours under nitrogen
  3. extractionextracted with EtOAc (2×15 mL)
  4. customOrganic layers were collected
  5. dry with materialcombined dried over anhydrous Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-42ba0f2ec884459282f30399febeab8b
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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