Sodium Hydroxide → 1-(3-Bromophenyl)piperidine-4-carboxylic acid

HRID 1852911Notes

Reaction equation

HRID 1852911 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([O:16]CC)=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:9][CH2:10][CH:11]([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71138417HCID 71138417, compound

Product 1

HCID 695708831-(3-Bromophenyl)piperidine-4-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 1-(3-bromophenyl)piperidine-4-carboxylate (5.6 g, 18 mmol) in THF/MeOH (360 mL, 1:1), was added a solution of NaOH (1M, 90 mL) at rt. The mixture was heated at 50° C. for 30 min and organic solvent was removed under reduced pressure. The water solution was mixed with ice and 1M HCl (90 mL) and extracted with dichloromethane/methanol. The combined organic phase was dried over unhydrous Na2SO4 and evaporated. The residue was solidified with dichloromethane/hexane to give the titled compound (4.4 g, 85%) as a white solid.

Workup

  1. customorganic solvent was removed under reduced pressure
  2. additionThe water solution was mixed with ice and 1M HCl (90 mL)
  3. extractionextracted with dichloromethane/methanol
  4. dry with materialThe combined organic phase was dried over unhydrous Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-85894c47796a460b99c315da727d0972
Source dataset
uspto-grants-2015_02
Patent number
US08962619B2

Reaction notes

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