Carbon tetrabromide → HCID 67322062, compound

HRID 1846635Notes

Reaction equation

HRID 1846635 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[C:5]([NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22]O)[CH2:17][CH2:16]1)=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:47]>C(Cl)Cl>[Br:47][CH2:22][CH2:21][CH:18]1[CH2:19][CH2:20][N:15]([C:9]2[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:8]=2[NH:7][C:5](=[O:6])[C:4]2[CH:24]=[CH:25][CH:26]=[C:2]([Cl:1])[CH:3]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67323243HCID 67323243, compound

Product 1

HCID 67322062HCID 67322062, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 0.800 g (2.03 mmol) of 3-chloro-N-{5-chloro-2-[4-(2-hydroxy-ethyl)-piperidin-1-yl]-phenyl}-benzamide and 0.533 g (2.03 mmol) of triphenylphosphine in methylene chloride (20 mL), cooled to 0° C., is stirred for 20 minutes. To this is added 0.674 g (2.03 mmol) of carbon tetrabromide and the mixture is warmed to room temperature and stirred overnight. The mixture is concentrated under reduced pressure and the residue is purified by flash silica gel chromatography to provide 0.400 g (70.0%) of N-{2-[4-(2-bromo-ethyl)-piperidin-1-yl]-5-chloro-phenyl}-3-chloro-benzamide as a light red oil.

Workup

  1. temperaturethe mixture is warmed to room temperature
  2. stirringstirred overnight
  3. concentrationThe mixture is concentrated under reduced pressure
  4. customthe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-dd4c26df92c04bd18c7a1b52a623c493
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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