Triethylamine → 4-[2-[4-(4-Pyridyl)piperazin-2-one-1-yl]acetyl]phenoxyacetic acid monohydrochloride

HRID 1291893Notes

Reaction equation

HRID 1291893 reaction equation
[N:1]1([CH2:8][C:9]([C:11]2[CH:22]=[CH:21][C:14]([O:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:13][CH:12]=2)=[O:10])[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].Cl.[Cl:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>O.O1CCOCC1>[ClH:24].[N:28]1[CH:29]=[CH:30][C:25]([N:4]2[CH2:5][CH2:6][N:1]([CH2:8][C:9]([C:11]3[CH:22]=[CH:21][C:14]([O:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:12]=3)=[O:10])[C:2](=[O:7])[CH2:3]2)=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 818524-Chloropyridine hydrochlorideHCID 18918321Methyl 4-[2-(piperazin-2-one-1-yl)acetyl]-phenoxyacetate

Product 1

HCID 700791174-[2-[4-(4-Pyridyl)piperazin-2-one-1-yl]acetyl]phenoxyacetic acid monohydrochlorideYield 40.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 4-[2-(piperazin-2-one-1-yl)acetyl]phenoxyacetate (0.347 g), 4-chloropyridine hydrochloride (0.19 g) and triethylamine (0.178 g) in water (8 ml) and dioxan (1 ml) was heated on a steam bath for 2 hours and then evaporated to dryness. The residue was triturated with water (2 ml) and filtered. The solid thus obtained was recrystallised from water to give the title compound (0.187 g), m.p. 275°-277° C.; NMR(d6DMSO δ8.33(2H,d), 8.0(2H,d), 7.21(2H,d), 7.1(2H,d), 4.97(2H,s), 4.81(2H,s), 3.94(2H,m), 3.59(2H,m); m/e 370(M+H)+ ; calculated for C19H20N3O5Cl. 0.75 H2O: C, 54.4; H, 5.0; N, 10.0. Found: C, 54.5; H, 5.3; N, 9.5%.

Workup

  1. customevaporated to dryness
  2. customThe residue was triturated with water (2 ml)
  3. filtrationfiltered
  4. customThe solid thus obtained
  5. customwas recrystallised from water

Sources & evidence

ORD record
ord-e7dcb16313874d9f9ad7220633f86103
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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