Triphenylphosphine → 1-[2-(4-Bromo-3-fluorophenoxy)ethyl]-4-methylpiperazine

HRID 874501Notes

Reaction equation

HRID 874501 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:29][N:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37]O)[CH2:32][CH2:31]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:37][CH2:36][N:33]2[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]2)=[CH:4][C:3]=1[F:9]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineHCID 27791534-Bromo-3-fluorophenol

Product 1

HCID 590006751-[2-(4-Bromo-3-fluorophenoxy)ethyl]-4-methylpiperazineYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask was charged with 4-bromo-3-fluorophenol (5.00 g, 26 mmol) and triphenylphosphine (10.30 g, 39 mmol). Methylene chloride (120 mL) was added followed by 2-(4-methylpiperazin-1-yl)ethanol (4.61 g, 32 mmol) and the solution was stirred on an ice water bath to cool. After 5 minutes, diisopropyl azodicarboxylate (7.6 ml, 39.1 mmol) was added over 6 to 8 minutes. The reaction was left stirring on the cold bath to slowly warm to room temperature overnight. The reaction was concentrated and the residue purified by flash chromatography (25% to 100% EtOAc in hexanes) to provide the product as a colorless oil (2.62 g, 33%).

Workup

  1. temperatureto cool
  2. waitThe reaction was left
  3. stirringstirring on the cold bath
  4. concentrationThe reaction was concentrated
  5. customthe residue purified by flash chromatography (25% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-12e16bd8decb4e6eb47233cbe9c5c50f
Source dataset
uspto-grants-2015_03
Patent number
US08980890B2

Reaction notes

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