Boron tribromide → 2-(4-Benzyl-piperidin-1-yl)-N-(4-hydroxy-phenyl)-acetamide

HRID 2115115Notes

Reaction equation

HRID 2115115 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=2)=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)=[O:16])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 2654155HCID 2654155, compound

Product 1

HCID 99451292-(4-Benzyl-piperidin-1-yl)-N-(4-hydroxy-phenyl)-acetamideYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 0.68 g (2 mmol) of 2-(4-benzyl-piperidin-1-yl)-N-(4-methoxy-phenyl)-acetamide (Example 190) and in 30 ml of dichloromethane 0.95 ml (10 mmol) of boron tribromide in 9 ml of dichloromethane is added dropwise at −20° C., and the reaction mixture is stirred at room temperature for 10 hours. The reaction mixture is concentrated. Then 30 ml of 8% sodium hydrogenecarbonate solution and 20 ml of chloroform are added to the mixture. The organic layer is separated and the water phase is extracted three times with 20 ml of chloroform. The combined organic layers are dried over sodium sulfate, concentrated and the residue is purified by column chromatography using Kieselgel 60 as adsorbent (Merck) and chloroform:methanol=9:1 as eluent to yield 0.4 g (62%) of the title compound. Melting Point: 66-70° C. (hexane)

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionThen 30 ml of 8% sodium hydrogenecarbonate solution and 20 ml of chloroform are added to the mixture
  3. customThe organic layer is separated
  4. extractionthe water phase is extracted three times with 20 ml of chloroform
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-c2dff6db9b6a4282a59cff24dcb40115
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

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