Boron tribromide → N-{2-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethyl}-3-hydroxybenzamide hydrochloride

HRID 1059016Notes

Reaction equation

HRID 1059016 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[Cl:29])[O:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=2)[CH2:9][CH2:8]1.B(Br)(Br)Br>ClCCl>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[Cl:29])[O:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22322410N-{2-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethyl}-3-methoxybenzamide hydrochloride

Product 1

HCID 22322198N-{2-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethyl}-3-hydroxybenzamide hydrochlorideYield 137.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The product of Example 10 (0.15 g) was dissolved in dichloromethane (10 ml) and a solution of 1.0M BBr3 in dichloromethane (4 ml) added. After 16 hours at room temperature the solvent was removed by evaporation, methanol was added and the solution concentrated. The residue was dissolved in 2M aqueous HCl solution, concentrated to dryness and the residue triturated under ether to give the titled product as a solid (0.1 g).

Workup

  1. customAfter 16 hours at room temperature the solvent was removed by evaporation, methanol
  2. additionwas added
  3. concentrationthe solution concentrated
  4. dissolutionThe residue was dissolved in 2M aqueous HCl solution
  5. concentrationconcentrated to dryness
  6. customthe residue triturated under ether

Sources & evidence

ORD record
ord-21d9a418f6b04a7d806c708bf18d9704
Source dataset
uspto-grants-2003_02
Patent number
US06518286B1

Reaction notes

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