Piperidin-4-ol → HCID 86680290, compound

HRID 2202599Notes

Reaction equation

HRID 2202599 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[N:11]([CH3:15])[N:12]=[CH:13][CH:14]=2)[OH:9])=[CH:4][CH:3]=1.O[CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:10]2[N:11]([CH3:15])[N:12]=[CH:13][CH:14]=2)[O:9][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 521998p-Toluenesulfonic acid monohydrateHCID 11550333HCID 11550333, compound

Product 1

HCID 86680290HCID 86680290, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2.074 g of (±)-(4-chlorophenyl)(2-methyl-2H-pyrazol-3-yl)methanol synthesized in Production Example 174, 942 mg of 4-hydroxypiperidine, 1.949 g of p-toluenesulfonic acid monohydrate, and 100 mL of toluene was heated under reflux for 40 minutes while removing water using a Dean-Stark. To the mixture, 1.949 g of p-toluenesulfonic acid monohydrate was added, and the resulting mixture was further heated under reflux for 4.3 hours while removing water. After the mixture was allowed to cool down, toluene and 22 mL of a 1-N sodium hydroxide aqueous solution were added thereto, and the organic layer was collected by separation. The organic layer was washed with 22 mL of a 1-N sodium hydroxide aqueous solution and with a saturated saline solution in this order. The organic layer was dried over sodium sulfate, and then the solvent was distilled off. Thus, the title compound (2.487 g (87%)) was obtained.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 40 minutes
  3. customwhile removing water using a Dean-Stark
  4. additionTo the mixture, 1.949 g of p-toluenesulfonic acid monohydrate was added
  5. temperaturethe resulting mixture was further heated
  6. temperatureunder reflux for 4.3 hours
  7. customwhile removing water
  8. temperatureto cool down
  9. additiontoluene and 22 mL of a 1-N sodium hydroxide aqueous solution were added
  10. customthe organic layer was collected by separation
  11. washThe organic layer was washed with 22 mL of a 1-N sodium hydroxide aqueous solution and with a saturated saline solution in this order
  12. dry with materialThe organic layer was dried over sodium sulfate
  13. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-0725a6fac8964d23b4e647ade34c0ed2
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

Loading…