Sodium Hydroxide → 4-[4-[4-(4-Pyridyl)piperazin-1-yl]phenoxy]butyric acid

HRID 1290488Notes

Reaction equation

HRID 1290488 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[OH-:20].[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:13][CH2:14][CH2:15][C:16]([OH:19])=[O:20])=[CH:15][CH:14]=3)[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 149869034-(4-(4-Pyridyl)piperazin-1-yl)phenol

Product 1

HCID 189185114-[4-[4-(4-Pyridyl)piperazin-1-yl]phenoxy]butyric acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of Example 50 (0.1 g) in aqueous sodium hydroxide (1N, 0.8 ml) and ethanol (2 ml) was kept for 2 hours. The solution was evaporated and the residue dissolved in water (5 ml). Hydrochloric acid (1N, 0.8 ml) was added and the precipitate was filtered and washed with water and ether to give the title compound as a solid: m.p. 305°-306° C.; m/e 342 (M+H)+ ; NMR (d6DMSO) δ 8.0(2H,d), 6.72(6H1,m); 3.74(2H,t); 3.3(4H,m); 2.94(4H,m); 2.19(2H,t); 1.72(2H,m); calculated for C19H23N3O3 : C, 66.8; H, 6.8; N, 12.3. Found: C, 67.0; H, 6.8; N, 12.2%.

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue dissolved in water (5 ml)
  3. additionHydrochloric acid (1N, 0.8 ml) was added
  4. filtrationthe precipitate was filtered
  5. washwashed with water and ether

Sources & evidence

ORD record
ord-0465e673848f456ba1bd09489d53b688
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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