Piperidin-4-ol → HCID 66750857, compound

HRID 534959Notes

Reaction equation

HRID 534959 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](OCC(Cl)(Cl)Cl)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[NH:25]1[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]1.C(N(C(C)C)C(C)C)C.C([O-])(O)=O.[Na+]>CS(C)=O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([N:25]2[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 66751339HCID 66751339, compound

Product 1

HCID 66750857HCID 66750857, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2,2,2-trichloroethyl 4-(2-tert-butylphenyl)piperazine-1-carboxylate (Example 60, 0.40 g, 1.02 mmol), piperidin-4-ol (0.50 g, 4.94 mmol), and N-ethyl-N-(1-methylethyl)propan-2-amine (0.158 g, 1.22 mmol) in DMSO (5 mL) was stirred for 3 days at 110° C. The reaction mixture was poured into saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to give a crude product. The product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=50:50 to 0:100 then ethyl acetate/methanol=100/0 to 70/30) to provide 1-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}piperidin-4-ol (0.121 g, 34%) as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated under reduced pressure
  5. customto give a crude product
  6. customThe product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=50:50 to 0:100

Sources & evidence

ORD record
ord-65e70094ced54deaa5d47776f488fc7e
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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