Triethylamine → 1-Cyclopropanecarbonyl-4-hydroxypiperidine

HRID 1654794Notes

Reaction equation

HRID 1654794 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[CH:15]1([C:18](Cl)=[O:19])[CH2:17][CH2:16]1>ClCCl>[CH:15]1([C:18]([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)=[O:19])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 79341Piperidin-4-ol

Product 1

HCID 149949671-Cyclopropanecarbonyl-4-hydroxypiperidineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

20 g of 4-hydroxypiperidine was dissolved in 400 ml of dichloromethane, to which 24 g of triethylamine was added. At -60° C., 100 ml of a dichloromethane solution containing 20.7 g of cyclopropanecarbonyl chloride was further added. After completion of the reaction, the reaction solution was extracted with chloroform under salting-out conditions and dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by the use of silica gel column chromatography (elution solvent:dichloroethane), thereby obtaining 32 g of the intended compound (yield 96%).

Workup

  1. additionwas added
  2. additionwas further added
  3. customAfter completion of the reaction
  4. extractionthe reaction solution was extracted with chloroform under salting-out conditions
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resultant residue was purified by the use of silica gel column chromatography (elution solvent:dichloroethane)

Sources & evidence

ORD record
ord-02724fe72730426590e5ab5b0fcc3479
Source dataset
uspto-grants-1995_04
Patent number
US05409909

Reaction notes

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