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

HRID 496876Notes

Reaction equation

HRID 496876 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-909116f1b5e34b13aa55e6ba8a663aa5
Source dataset
uspto-grants-2005_09
Patent number
US06946478B2

Reaction notes

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