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

HRID 1161664Notes

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

Participants

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

extractionextracted with ethyl acetate (3×50 mL)
customThe organic layers were collected
washwashed with water (50 mL)
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated under vacuum
customThe residue thus obtained
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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