4-(4-Methylbenzyl)-piperidin-4-ol → HCID 22628365, compound

HRID 278446Notes

Reaction equation

HRID 278446 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[CH2:7][CH:8]([CH2:10]OS(C3C=CC(C)=CC=3)(=O)=O)[O:9][C:5]=2[CH:4]=1.[CH3:24][C:25]1[CH:38]=[CH:37][C:28]([CH2:29][C:30]2([OH:36])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:27][CH:26]=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[CH2:7][CH:8]([CH2:10][N:33]3[CH2:34][CH2:35][C:30]([CH2:29][C:28]4[CH:27]=[CH:26][C:25]([CH3:24])=[CH:38][CH:37]=4)([OH:36])[CH2:31][CH2:32]3)[O:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 105362424-(4-Methylbenzyl)-piperidin-4-olHCID 54378120HCID 54378120, compound

Product 1

HCID 22628365HCID 22628365, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

(RS)-toluene-4-sulfonic acid 6-methoxy-2,3-dihydro-benzofuran-2-ylmethyl ester (110 mg, 0.33 mmol) and 4-(4-methyl-benzyl)-piperidin-4-ol (148 mg, 0.72 mmol) were dissolved in DMF (3 ml) and heated at 130° C. for 1 h. DMF was then evaporated, the residue was dissolved in CH2Cl2 (5 ml) and washed with H2O (5 ml). Organic phase was dried over Na2SO4, and concentrated. The residue was chromatographed over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2-MeOH(19:1) to provide (RS)-1-(6-methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol (80 mg, 66%) as a yellow oil, MS:m/e=368.4 (M+H+).

Workup

  1. customDMF was then evaporated
  2. dissolutionthe residue was dissolved in CH2Cl2 (5 ml)
  3. washwashed with H2O (5 ml)
  4. dry with materialOrganic phase was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed over SiO2 (Merck 230-400 mesh)
  7. washeluting with CH2Cl2-MeOH(19:1)

Sources & evidence

ORD record
ord-8c4f294590064ef89c266db3166a678a
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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