Potassium tert-butoxide → 1-[2-(2-Hydroxyethyl)phenyl]piperidin-2-one

HRID 2178517Notes

Reaction equation

HRID 2178517 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][OH:17])=[O:7].CC(C)([O-])C.[K+]>C1COCC1>[OH:17][CH2:16][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:8]1[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1=[O:7]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 895005435-bromo-N-[2-(2-hydroxyethyl)phenyl]pentanamide

Product 1

HCID 895002661-[2-(2-Hydroxyethyl)phenyl]piperidin-2-oneYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromo-N-[2-(2-hydroxyethyl)phenyl]pentanamide a2-1 (938 g, 3.28 mol, 1 eq) in THF (6 l) is cooled at −5° C. Potassium tert-butoxide (552 g, 4.92 mol, 1.5 eq) is added portionwise, without exceeding 0° C., then the mixture is warmed up to room temperature. The reaction mixture is washed with a saturated aqueous solution of NaCl (3×2 l). The aqueous layers are extracted with dichloromethane (2×2 l), the combined organic layers are dried over MgSO4, filtered and condensed under reduced pressure. The residue is recrystallized from tert-butyl methyl ether to afford 510 g of 1-[2-(2-hydroxyethyl)phenyl]piperidin-2-one a2-2.

Workup

  1. customwithout exceeding 0° C.
  2. washThe reaction mixture is washed with a saturated aqueous solution of NaCl (3×2 l)
  3. extractionThe aqueous layers are extracted with dichloromethane (2×2 l)
  4. dry with materialthe combined organic layers are dried over MgSO4
  5. filtrationfiltered
  6. customcondensed under reduced pressure
  7. customThe residue is recrystallized from tert-butyl methyl ether

Sources & evidence

ORD record
ord-d941de83038a40a09fff5a422727109a
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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