Sodium Hydroxide → HCID 69055012, compound

HRID 1727210Notes

Reaction equation

HRID 1727210 reaction equation
C([C:4]1([CH:12]=[CH:11][C:10]([CH2:13][O:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:9][CH2:8]1)[C:5]([OH:7])=[O:6])(=O)C.[OH-].[Na+]>CO>[NH:18]1[CH2:17][CH2:16][CH:15]([O:14][CH2:13][C:10]2[CH:11]=[CH:12][C:4]([C:5]([OH:7])=[O:6])=[CH:8][CH:9]=2)[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69057098HCID 69057098, compound

Product 1

HCID 69055012HCID 69055012, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-acetyl-4-[(piperidin-4-yloxy)methyl]benzoic acid (Preparation 102, 20 g, 72 mmol), aqueous sodium hydroxide solution (5 M, 75 ml), and methanol (75 ml) were heated to 100° C. for 4 h, and then evaporated to give a thick suspension. The crystals were filtered off, dissolved in water and the pH adjusted to 1 with hydrochloric acid (2 M, 200 ml) at 0° C. The cloudy solution was evaporated to dryness and the white solid recrystallised from isopropyl alcohol to give the title compound (15.2 g, 90%).

Workup

  1. customevaporated
  2. customto give a thick suspension
  3. filtrationThe crystals were filtered off
  4. dissolutiondissolved in water
  5. customadjusted to 1 with hydrochloric acid (2 M, 200 ml) at 0° C
  6. customThe cloudy solution was evaporated to dryness
  7. customthe white solid recrystallised from isopropyl alcohol

Sources & evidence

ORD record
ord-7c00bdd580c64d09b7fcfa0e6245fffa
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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