Phosphorus tribromide → 1-(3-Bromopentyl)-4-(diphenylmethyl)piperazine

HRID 2297528Notes

Reaction equation

HRID 2297528 reaction equation
[C:1]1([CH:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16](O)[CH2:17][CH3:18])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:27].C(=O)([O-])O.[Na+]>C1C=CC=CC=1.CCOCC>[Br:27][CH:16]([CH2:17][CH3:18])[CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][N:8]([CH:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 183819271-(4-(Diphenylmethyl)piperazinyl)pentane-3-ol

Product 1

HCID 183819191-(3-Bromopentyl)-4-(diphenylmethyl)piperazineYield 31%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

1-(4-(diphenylmethyl)piperazinyl)pentane-3-ol (940 mg) was dissolved in benzene (10 ml) and ether (10 ml), and then phosphorus tribromide (0.2 ml) was added thereto, followed by stirring the mixture overnight at room temperature. To the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was added and the resultant was extracted 3 times with ethyl acetate. Organic layers were combined and washed with brine. The resultant was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 340 mg of 1-(3-bromopentyl)-4-(diphenylmethyl)piperazine. Yield: 31%.

Workup

  1. extractionthe resultant was extracted 3 times with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe resultant was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-5e72f128c84f4de18cac99cd03f8e0e3
Source dataset
uspto-grants-2002_12
Patent number
US06492364B1

Reaction notes

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