Water → 1-[(4-bromophenyl)sulfonyl]-4-piperidinecarboxylic acid

HRID 1936567Notes

Reaction equation

HRID 1936567 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]([O:21]CC)=[O:20])[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.O>C(O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([N:13]2[CH2:14][CH2:15][CH:16]([C:19]([OH:21])=[O:20])[CH2:17][CH2:18]2)(=[O:12])=[O:11])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 1219636HCID 1219636, compound

Product 1

HCID 7378431-[(4-bromophenyl)sulfonyl]-4-piperidinecarboxylic acidYield 94.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide solution (100 ml at 40% w/v) was added to a stirred suspension of the above ester (78.0 g) in ethanol (200 ml)/water (100 ml). Water (100 ml) was added and the reaction mixture heated to reflux and reflux maintained for 30 minutes. The reaction mixture was cooled and the crystalline sodium salt was collected. This sodium salt was suspended in water (350 ml) and glacial acetic acid added to adjust the pH of the solution to 5. The mixture was stirred for 1 hour and the colourless solid collected, washed with water and dried to give, as a colourless solid, 1-(4-bromophenylsulphonyl)piperidine-4-carboxylic acid (68.4 g): m.p. 225-227° C.; microanalysis, found: C, 41.0; H, 3.7; N, 3.9%; C12H14BrNO4S requires: C, 41.4; H, 4.1; N 4.0%; NMR: 1.41-1.63(m, 2H), 1.73-1.93(m, 2H), 2.11-2.30(m, 1H), 2.44(t, 2H); 3.28-3.60(m, 2H), 7.62(d, 2H) 7.89(d, 2H).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux
  3. temperaturereflux
  4. temperaturemaintained for 30 minutes
  5. temperatureThe reaction mixture was cooled
  6. customthe crystalline sodium salt was collected
  7. additionglacial acetic acid added
  8. customthe colourless solid collected
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-725ffd90fb9546b4a680a4a92fc181c4
Source dataset
uspto-grants-2002_05
Patent number
US06391880B1

Reaction notes

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