4-Benzyl-4-piperidinol → 1-[2-(4-Benzyl-4-hydroxy-piperidin-1-yl)-ethyl]-3-(2,6-dimethyl-pyridin-4-yl)-urea

HRID 2354074Notes

Reaction equation

HRID 2354074 reaction equation
[CH2:1]([C:8]1([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].Cl[CH2:21][CH2:22][NH:23][C:24]([NH:26][C:27]1[CH:32]=[C:31]([CH3:33])[N:30]=[C:29]([CH3:34])[CH:28]=1)=[O:25]>C1COCC1>[CH2:1]([C:8]1([OH:14])[CH2:13][CH2:12][N:11]([CH2:21][CH2:22][NH:23][C:24]([NH:26][C:27]2[CH:32]=[C:31]([CH3:33])[N:30]=[C:29]([CH3:34])[CH:28]=2)=[O:25])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 981524-Benzyl-4-piperidinolHCID 516892Sodium BicarbonateHCID 588165671-(2-Chloro-ethyl)-3-(2,6-dimethyl-pyridin-4-yl)-urea

Product 1

HCID 114404691-[2-(4-Benzyl-4-hydroxy-piperidin-1-yl)-ethyl]-3-(2,6-dimethyl-pyridin-4-yl)-urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of commercially available 4-benzyl-piperidin-4-ol (383 mg, 2.0 mmol). NaHCO3 (672 mg, 8.0 mmol) and 1-(2-chloro-ethyl)-3-(2,6-dimethyl-pyridin-4-yl)-urea (Example D1., 227.7 mg 1.0 mmol) in THF (4 mL) is stirred at 50° C. for 4 days. The mixture is quenched with Na2CO3 (10 mL) and extracted with CH2Cl2 (3×10 mL). The organic extracts are washed with sat. aq. Na2CO3 (10 mL), dried (Na2SO4), filtered and evaporated. The residue is purified by HPLC to provide the title compound.

Workup

  1. customThe mixture is quenched with Na2CO3 (10 mL)
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. washThe organic extracts are washed with sat. aq. Na2CO3 (10 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-d0875af3d9e64d01a22bcd9457551d47
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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