Water → 1-Benzyl-4-(hydroxymethyl)piperidin-4-ol

HRID 47336Notes

Reaction equation

HRID 47336 reaction equation
O.Cl(O)(=O)(=O)=O.[CH2:7]([N:14]1[CH2:22][CH2:21][C:17]2([C:19](=[O:20])C2)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-:24].[Na+].[Na+]>O1CCCC1>[CH2:7]([N:14]1[CH2:22][CH2:21][C:17]([CH2:19][OH:20])([OH:24])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24247Perchloric AcidHCID 227445766-Benzyl-1-oxo-6-azaspiro[2.5]octane

Product 1

HCID 140253361-Benzyl-4-(hydroxymethyl)piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 ml water and 10 ml perchloric acid were added to 100 ml solution of 6.8 g of this 6-benzyl-1-oxo-6-azaspiro[2.5]octane in tetrahydrofuran, and the mixture was stirred at room temperature for 7 hr. The mixture was ice-cooled, and aqueous sodium carbonate was added thereto to adjust the pH thereof to 7, and then the mixture was evaporated. Ethyl acetate was added to the residue, and the insoluble mattters were removed by filtration. The filtrate was evaporated, and then purified by silica gel column chromatography to give 4 g of 1-benzyl-4-(hydroxymethyl)-4-piperidinol.

Workup

  1. temperaturecooled
  2. customto 7, and then the mixture was evaporated
  3. additionEthyl acetate was added to the residue
  4. customthe insoluble mattters were removed by filtration
  5. customThe filtrate was evaporated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-850a417da94f434687c292e4d1a8c03c
Source dataset
uspto-grants-2004_03
Patent number
US06699870B2

Reaction notes

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