Boron tribromide → HCID 23441027, compound

HRID 2119353Notes

Reaction equation

HRID 2119353 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:10][CH2:11][N:12]2[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=3)[CH2:14][CH2:13]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:10][CH2:11][N:12]2[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=3)[CH2:14][CH2:13]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 23441040HCID 23441040, compound

Product 1

HCID 23441027HCID 23441027, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 mL solution in dichloromethane of 33 mg of 1-[3-(4-methoxyphenyl)3-phenyl propyl]-4-[4-(methylsulfonyl)benzyl]homopiperazine was cooled under nitrogen to −78° C. followed by adding 0.022 mL of boron tribromide. The mixture was gradually allowed to rise to room temperature, at which temperature the mixture was stirred for 3 hours, followed by adding 3 mL of an aqueous saturated sodium hydrogencarbonate solution and extracting with a 50 mL×2 of ethyl acetate. The extracts were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography (silica gel, ethyl acetate/methanol 9:1) to obtain 12 mg of the titled compound. This was treated with a hydrogen chloride solution in ether and the solvent was removed under reduced pressure and residue was dried to give the hydrochloride salt of the titled compound.

Workup

  1. customto rise to room temperature, at which temperature
  2. extractionextracting with a 50 mL×2 of ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica gel, ethyl acetate/methanol 9:1)

Sources & evidence

ORD record
ord-222bdf7378e6414fa45e15971b7a9824
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

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