Sodium hydride → 1-(3,5-Di-tert-butyl-4-hydroxyphenyl)piperidin-2-one

HRID 1613271Notes

Reaction equation

HRID 1613271 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:16][C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21]Cl)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+]>O1CCCC1>[C:1]([C:5]1[CH:6]=[C:7]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=[O:23])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 19775707N-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-chlorovaleramide

Product 1

HCID 148520221-(3,5-Di-tert-butyl-4-hydroxyphenyl)piperidin-2-oneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-chlorovaleramide (5.5 g: 16 mmol) in 25 ml of tetrahydrofuran was slowly added to 1.4 g (35 mmol) of 60% sodium hydride in mineral oil (washed twice with 25 ml portions of hexane) and 50 ml of tetrahydrofuran. The reaction mixture was stirred and gas evolution was observed. Seventeen hours later the mixture was concentrated to 20 ml, diluted with 50 ml of methylene chloride and washed successively with dilute 1N hydrochloric acid and dilute sodium bicarbonate solution. The organic phase was dried over anhydrous magnesium sulfate and concentrated to a solid (4.5 g). This solid was recrystallized from acetone to yield 3.9 g (12.8 mmol, 80%) of crystalline 1-(3,5-di-tert-butyl-4-hydroxyphenyl)piperidin-2-one, mp 212°-214° C.

Workup

  1. washwashed twice with 25 ml portions of hexane) and 50 ml of tetrahydrofuran
  2. concentrationSeventeen hours later the mixture was concentrated to 20 ml
  3. additiondiluted with 50 ml of methylene chloride
  4. washwashed successively
  5. additionwith dilute 1N hydrochloric acid and dilute sodium bicarbonate solution
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated to a solid (4.5 g)
  8. customThis solid was recrystallized from acetone

Sources & evidence

ORD record
ord-bf8a7fbdeaa74b07bb55eb3bc201de7a
Source dataset
uspto-grants-1993_03
Patent number
US05192791

Reaction notes

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