Piperidin-4-ol → HCID 60137850, compound

HRID 1855434Notes

Reaction equation

HRID 1855434 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[OH:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([N:14]2[CH2:15][CH2:16][CH:11]([OH:10])[CH2:12][CH2:13]2)[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

4

Reactant 2

HCID 79341Piperidin-4-olHCID 794712,4-Dichloro-6-methylpyrimidine

Product 1

HCID 60137850HCID 60137850, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dichloro-6-methylpyrimidine (998 mg, 6.0 mmol) in tetrahydrofurane (30 mL) was added under stirring N,N-diisopropyl ethyl amine (853 mg, 6.6 mmol) and 4-hydroxypiperidine (681 mg, 6.6 mmol) and the reaction was stirred over night at 20° C. The solvent was evaporated under reduced pressure and the residue was taken up in water and extracted twice with diethyl ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure to dryness. The residue was purified by column chromatography on silica gel using heptane/ethyl acetate (1:1 v/v) as eluent to yield the title compound (779 mg, 57%) as white crystals. MS ISP (m/e): 228.2/230.2 (100/35) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=6.73 (s, 1H), 4.78 (d, 1H), 3.95 (br m, 2H), 3.75 (m, 1H), 3.25 (m, 2H), 2.22 (s, 3H), 1.75 (m, 2H), 1.33 (m, 2H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionextracted twice with diethyl ether
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure to dryness
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d1ae1b5260f543728ab6aa6a33824758
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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