Hydrochloric Acid → HCID 21914372, compound

HRID 2421373Notes

Reaction equation

HRID 2421373 reaction equation
CC1C=CC(S([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[C:14]([O:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:13]=2)(=O)=O)=CC=1.[OH-].[K+].Cl.C(=O)(O)[O-].[Na+]>C(O)C.O>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([OH:11])=[CH:13][C:14]=1[O:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 21914252HCID 21914252, compound

Product 1

HCID 21914372HCID 21914372, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Bromo-3-(2-{piperidin-1-yl}ethoxy)phenyl 4-methylbenzenesulfonate (24.2 g), potassium hydroxide (16.1 g), water (96 ml) and ethanol (860 ml) were heated on the steam bath for 2 h. The pH was adjusted to 4 with concentrated hydrochloric acid, then to pH 7 with solid sodium bicarbonate. After evaporation to near dryness, water (200 ml) was added and the mixture was extracted with ethyl acetate (3×150 ml). The organic phase was washed with water, brine, dried (MgSO4) and evaporated to give an oil (16.4 g).

Workup

  1. customAfter evaporation
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate (3×150 ml)
  4. washThe organic phase was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-32803d3539da4925b6e7ded171a99a6c
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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