Butyl bromide → 1-Butyl-3-piperidinemethanol

HRID 400213Notes

Reaction equation

HRID 400213 reaction equation
[OH-].[Na+].[NH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9][OH:10])[CH2:4]1.[CH2:11](Br)[CH2:12][CH2:13][CH3:14]>C(O)C>[CH2:11]([N:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9][OH:10])[CH2:4]1)[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 14798Sodium HydroxideHCID 107308Piperidin-3-ylmethanol

Product 1

HCID 184737241-Butyl-3-piperidinemethanolYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A] A 1N solution of sodium hydroxide (174 ml, 0.17 mole) was added to a mixture of 3-piperidinemethanol (20 g, 0.17 mole) and butyl bromide (23 ml, 0.2 mole) in ethanol (200 ml). The reaction mixture was refluxed for 4 hours, then the solvent was evaporated under vacuum. The aqueous solution was acidified with HCl and washed with ethyl ether, then treated with a 32% solution of sodium hydroxide to pH-12 and extracted with ethyl ether. The combined organic phases were anhydrified over sodium sulfate and the solvent was evaporated under vacuum. The crude was purified by distillation yielding 23 g of N-butyl-3-piperidinemethanol (b.p.: 115-117/6 mmHg) (yield: 79%).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. customthe solvent was evaporated under vacuum
  3. washwashed with ethyl ether
  4. additiontreated with a 32% solution of sodium hydroxide to pH-12
  5. extractionextracted with ethyl ether
  6. customthe solvent was evaporated under vacuum
  7. distillationThe crude was purified by distillation

Sources & evidence

ORD record
ord-60b62c932961423e82ec2d077841921b
Source dataset
uspto-grants-1998_10
Patent number
US05827881

Reaction notes

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