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

HRID 637682Notes

Reaction equation

HRID 637682 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 mmole) of dicyclohexyl carbodiimide in 40 ml of absolute methylene chloride is added at room temperature over a period of approximately 3 minutes to a solution of 8.1 g (30 mmole) of crude 5-chloro-2-hydroxy-4-(piperidin-1-yl)-phenylacetic acid in 50 ml of absolute methylene chloride. The reaction mixture is stirred for 30 minutes at room temperature. The precipitated dicyclohexylurea is filtered 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 using methylene chloride/hexane (1:1) as eluant. recrystallisation from hexane yields 5-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one having a melting point of 129°-131°.

Workup

  1. filtrationThe precipitated dicyclohexylurea is filtered 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
  5. customrecrystallisation from hexane

Sources & evidence

ORD record
ord-1a867f40a79f4d23a8e7480012d19c6f
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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