Butyl bromide → HCID 18473723, compound

HRID 400215Notes

Reaction equation

HRID 400215 reaction equation
[OH-].[Na+].[NH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][CH2:10][OH:11].[CH2:12](Br)[CH2:13][CH2:14][CH3:15]>C(O)C>[CH2:12]([N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][CH2:10][OH:11])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 14798Sodium HydroxideHCID 151442-Piperidin-2-ylethanol

Product 1

HCID 18473723HCID 18473723, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A! A solution of 1N sodium hydroxide (156 ml, 0.156 mole) was added to a mixture of 2-piperidine-ethanol (20 ml, 0.156 mole) and butyl bromide (21 ml, 0.187 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 it was treated with a 32% solution of sodium hydroxide until pH-12 and extracted with ethyl ether. The combined organic phases were anhydrified over sodium sulfate and the solvent was evaporated under vacuum. The resulting crude was purified by distillation yielding 1.7 g of N-butyl-2-piperidine-ethanol (b.p.: 88°-99° C./0mmHg) (yield: 40%).

Workup

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

Sources & evidence

ORD record
ord-ad793f1392ec4814b457edd404b3012a
Source dataset
uspto-grants-1998_10
Patent number
US05827881

Reaction notes

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