Hydrochloric Acid → 3-[1-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]piperidin-4-yl]propanoic acid

HRID 1290501Notes

Reaction equation

HRID 1290501 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([N:16]3[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])[CH2:18][CH2:17]3)=[O:15])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.Cl>O1CCOCC1>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([CH2:13][C:14]([N:16]3[CH2:17][CH2:18][CH:19]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH2:20][CH2:21]3)=[O:15])[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18918542Ethyl 3-[1-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]piperidin-4-yl]propanoate

Product 1

HCID 189186023-[1-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]piperidin-4-yl]propanoic acidYield 103.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture containing ethyl 3-[1-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]piperidin-4-yl]propanoate (50 mg), concentrated hydrochloric acid (1 ml) and dioxan (4 ml) was stirred at 50°-60° C. for 1 hour,then concentrated to give a foam which was triturated with hot isopropanol. Filtration gave the title compound (48 mg) as pale cream prisms, m.p. 188°-190° C. NMR (d6DMSO+d4AcOH) δ1.0-1.3(2H,m); 1.5-1.6(3H,m); 1.8(2H,d); 2.3(2H,t); 2.6-2.8(1H,m); 2.95-3.15(1H,m); 3.5(4H,brs); 3.6-3.7(1H,m); 4.0-4.2(4H,brs); 4.3-4.5(3H,m); 7.25(2H,d); 8.35(2H,d); m/e 361(M+H)+ ; calculated for C19H28N4O3 2HCl. H2O: C,50.6;H, 7.2; N, 12.4; H2O, 4.0; found: C,50.3; H, 7.2; N, 12.2; H2O, 4.0%.

Workup

  1. concentrationconcentrated
  2. customto give a foam which
  3. customwas triturated with hot isopropanol
  4. filtrationFiltration

Sources & evidence

ORD record
ord-e07ed4d1e817424da693e9497790eb90
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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