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Water → 1-(2-Chloro-6-phenyl-pyrimidin-4-yl)-piperidin-4-ol

HRID 1161664
Notes
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Reaction equation

HRID 1161664 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]1.C(N(CC)CC)C.O>C(O)CCC>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=[C:2]([N:15]2[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]2)[N:7]=1.[Cl:1][C:2]1[N:7]=[C:6]([N:15]2[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]2)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 2415542,4-Dichloro-6-phenylpyrimidine

Product 2

HCID 586260781-(2-Chloro-6-phenyl-pyrimidin-4-yl)-piperidin-4-olHCID 586261271-(4-Chloro-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of compound, 2,4-dichloro-6-phenyl-pyrimidine (13 g, 57.77 mmol), piperidin-4-ol (2.9 g, 28.88 mmol) and triethylamine (32.14 mL, 231.11 mmol) in butanol (110 mL) was stirred at 120° C. for 12 hours under nitrogen atmosphere. The reaction mixture was then poured into water (250 mL) and extracted with ethyl acetate (3×50 mL). The organic layers were collected, combined, washed with water (50 mL), dried over anhydrous sodium sulphate, and concentrated under vacuum. The residue thus obtained was purified by column chromatography using ethyl acetate-petroleum ether to give the two compounds, 1-(4-chloro-6-phenyl-pyrimidin-2-yl)-piperidin-4-ol and 1-(2-chloro-6-phenyl-pyrimidin-4-yl)-piperidin-4-ol in ratio 1:4 (overall yield: 51%).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. customThe organic layers were collected
  3. washwashed with water (50 mL)
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under vacuum
  6. customThe residue thus obtained
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-58b9974ee23e462f936c2eca623109c8
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07820654B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes