Piperidin-4-ol → HCID 15675404, compound

HRID 1461274Notes

Reaction equation

HRID 1461274 reaction equation
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][CH:4]=1.[OH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>CN(C)C=O>[OH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:2][C:3]2[O:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][CH:4]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 79341Piperidin-4-olHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylate

Product 1

HCID 15675404HCID 15675404, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 45 ml of dimethylformamide was dissolved 6.0 g (31.8 mmol) of ethyl 5-chloromethyl-2-furancarboxylate followed by addition of 9.64 g (95.5 mmol) of 4-hydroxypiperidine and the mixture was stirred at room temperature for 20 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with 100 ml of chloroform and washed with saturated aqueous sodium chloride solution twice. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off to give 7.84 g (97.4%) of ethyl 5-(4-hydroxypiperidinomethyl)-2-furancarboxylate (Compound s) as light brown oil.

Workup

  1. distillationThe solvent was then distilled off under reduced pressure
  2. additionthe residue was diluted with 100 ml of chloroform
  3. washwashed with saturated aqueous sodium chloride solution twice
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-ca33547d971f4130b9762b3cb751fe0e
Source dataset
uspto-grants-1991_12
Patent number
US05075301

Reaction notes

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