Succinic anhydride → HCID 14986922, compound

HRID 1493585Notes

Reaction equation

HRID 1493585 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:37]=[CH:36][C:17]([O:18][CH2:19][C:20]([C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=4[Cl:35])([OH:27])[CH2:21][N:22]4[CH:26]=[N:25][CH:24]=[N:23]4)=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:38]1(=O)[O:43][C:41](=[O:42])[CH2:40][CH2:39]1>C(O)(=O)C>[Cl:35][C:29]1[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:28]=1[C:20]([OH:27])([CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1)[CH2:19][O:18][C:17]1[CH:36]=[CH:37][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:6]=[CH:7][C:2]([N:1]4[C:41](=[O:42])[CH2:40][CH2:39][C:38]4=[O:43])=[CH:3][CH:4]=3)[CH2:9][CH2:10]2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 14986929HCID 14986929, compound

Product 1

HCID 14986922HCID 14986922, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(4-[4-(4-aminophenyl)piperazin-1-yl]phenoxy)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (see Preparation 1) (0.2 g, 0.37 mmole) and succinic anhydride (0.05 g, 0.5 mmole) in acetic acid (3 ml) was heated under reflux for 4 hours. The solution was cooled, the solvent removed by concentration under reduced pressure and the resulting gum triturated with isopropanol to provide a solid (0.165 g). Purification of this solid material by flash chromatography on silica gel eluting with methylene chloride (90):isopropanol (10):acetic acid (1) yielded, after collection and evaporation of appropriate fractions, the desired product, m.p. 212°-216° (0.072 g, 31%).

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureThe solution was cooled
  3. customthe solvent removed by concentration under reduced pressure
  4. customthe resulting gum triturated with isopropanol

Sources & evidence

ORD record
ord-18c81a015d0a4df6aebbb42e1d06cf07
Source dataset
uspto-grants-1991_06
Patent number
US05023258

Reaction notes

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