Sulfuric Acid → 1-Benzyl-4-hydroxypiperidine-4-carboxamide

HRID 47313Notes

Reaction equation

HRID 47313 reaction equation
S(=O)(=O)(O)O.Cl.[CH2:7]([N:14]1[CH2:19][CH2:18][C:17]([OH:22])([C:20]#[N:21])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-:23].[Na+]>O>[CH2:7]([N:14]1[CH2:15][CH2:16][C:17]([OH:22])([C:20]([NH2:21])=[O:23])[CH2:18][CH2:19]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 14798Sodium HydroxideHCID 27237801-Benzyl-4-hydroxypiperidine-4-carbonitrile monohydrochloride

Product 1

HCID 227445201-Benzyl-4-hydroxypiperidine-4-carboxamideYield 68.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixed solution of 18 ml conc. sulfuric acid and 1.8 ml water was cooled to 0° C., and 5 g of 1-benzyl-4-hydroxy-4-piperidinecarbonitrile hydrochloride was added thereto little by little. A mixed solution of 25 ml conc. sulfuric acid and 2.5 ml water was added thereto, and stirred at room temperature for 2 hr. It was left overnight in a freezer. The reaction solution was poured onto ice, and 47 g of sodium hydroxide was added thereto little by little. It was extracted 3 times with a mixed solvent of tetrahydrofuran and ethyl acetate (1:1). The extract was washed with brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was evaporated and subjected to silica gel column chromatography to give 3.19 g of 1-benzyl-4-hydroxy-4-piperidine carboxamide.

Workup

  1. waitIt was left overnight in a freezer
  2. additionwas added
  3. extractionIt was extracted 3 times with a mixed solvent of tetrahydrofuran and ethyl acetate (1:1)
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-b9a7e5cfbefa49d788b5a9a52fbcdd47
Source dataset
uspto-grants-2004_03
Patent number
US06699870B2

Reaction notes

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