Dicyclohexylcarbodiimide → 5-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one

HRID 544714Notes

Reaction equation

HRID 544714 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[Cl:16][C:17]1[C:18]([N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:19][C:20]([OH:27])=[C:21]([CH2:23][C:24](O)=[O:25])[CH:22]=1>C(Cl)Cl>[Cl:16][C:17]1[C:18]([N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:19][C:20]2[O:27][C:24](=[O:25])[CH2:23][C:21]=2[CH:22]=1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 539130445-Chloro-2-hydroxy-4-(piperidin-1-yl)-phenylacetic acid

Product 1

HCID 135769525-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6.5 g (31.5 mmoles) of dicyclohexylcarbodiimide in 40 ml of absolute methylene chloride is added at room temperature in the course of approximately 3 minutes to a solution of 8.1 g (30 mmoles) of crude 5-chloro-2-hydroxy-4-(piperidin-1-yl)-phenylacetic acid in 50 ml of absolute methylene chloride. The reaction mixture is stirred at room temperature for 30 minutes. The precipitated dicyclohexylurea is filtered off with suction and washed with methylene chloride. The filtrate is concentrated by evaporation in a vacuum rotary evaporator and the residue is chromatographed over silica gel with the eluant methylene chloride/hexane (1:1). Recrystallisation from hexane yields 5-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one having a melting point of 129°-131° C.

Workup

  1. filtrationThe precipitated dicyclohexylurea is filtered off with suction
  2. washwashed with methylene chloride
  3. concentrationThe filtrate is concentrated by evaporation in a vacuum rotary evaporator
  4. customthe residue is chromatographed over silica gel with the eluant methylene chloride/hexane (1:1)
  5. customRecrystallisation from hexane

Sources & evidence

ORD record
ord-651c7a7cd4f84285988f9a7cb5b05936
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Reaction notes

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