2-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1) → HCID 70157124, compound

HRID 276965Notes

Reaction equation

HRID 276965 reaction equation
O.[C:2]([OH:14])(=[O:13])[CH2:3][C:4]([CH2:9][C:10]([OH:12])=[O:11])([C:6]([OH:8])=[O:7])[OH:5].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH2:23][CH2:24][N:25]([CH2:28][CH2:29][CH2:30][CH2:31][N:32]3[CH:36]=[N:35][CH:34]=[N:33]3)[CH2:26][CH:27]=2)=[CH:18][CH:17]=1>O.C(O)C>[C:2]([OH:14])(=[O:13])[CH2:3][C:4]([CH2:9][C:10]([OH:12])=[O:11])([C:6]([OH:8])=[O:7])[OH:5].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][CH2:30][CH2:31][N:32]3[CH:36]=[N:35][CH:34]=[N:33]3)[CH2:24][CH:23]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 18313764HCID 18313764, compound

Product 1

HCID 70157124HCID 70157124, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of citric acid monohydrate (33.8 g, 0.16 mol) in water (30 ml) is added to a solution of 4-(4-chlorophenyl)-1,2,3,6-tetrahydro-1-[4-(1H-1,2,4-triazol-1-yl)butyl]pyridine (51 g, 0.16 mol) in absolute ethanol (350 ml) at 40° C. After about 20 minutes a precipitate appears, which is filtered after cooling to room temperature, washed with cold ethanol and dried, yielding 68.9 g (84%) of 4-(4-chlorophenyl)-1,2,3,6-tetrahydro-1-[4-(1H-1,2,4-triazol-1-yl)butyl]pyridine citrate of m.p. 133-4° C.

Workup

  1. filtrationwhich is filtered
  2. washwashed with cold ethanol
  3. customdried

Sources & evidence

ORD record
ord-86526ee352614e32b5421feef0c1b86e
Source dataset
uspto-grants-2002_03
Patent number
US06355659B1

Reaction notes

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