Triphenylphosphine dibromide → HCID 19004128, compound

HRID 2226049Notes

Reaction equation

HRID 2226049 reaction equation
[C:1]1([N:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:28])[N:17]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:12][CH:11]2[CH2:29][CH2:30]O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:38]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[C:1]1([N:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:28])[N:17]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:12][CH:11]2[CH2:29][CH2:30][Br:38])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70579Triphenylphosphine dibromideHCID 19004138HCID 19004138, compound

Product 1

HCID 19004128HCID 19004128, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 312 mg (0.61 mmol) of (RS)-1-(N,N-diphenylcarbamoyl)-2-(2-hydroxyethyl)-4-(N,N-dipentylcarbamoyl)piperazine and 362 mL (0.86 mmol) of dibromotriphenylphosphorane in 15 mL of acetonitrile was stirred under nitrogen at 82° C. for 2 hours. The yellow solution was cooled and concentrated in vacuo. Flash chromatography on 35 g of silica gel using 1:1 v/v ethyl acetate/hexane as the eluant afforded 300 mg (85%) of a yellow oil.

Workup

  1. temperatureThe yellow solution was cooled
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-869f2241d08f4b25ab183155c1d0e1ac
Source dataset
uspto-grants-1994_09
Patent number
US05344830

Reaction notes

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