Propargyl bromide → DIPHENYL-PROP-2-YNYL-AMINE

HRID 1886488Notes

Reaction equation

HRID 1886488 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[CH2:16](Br)[C:17]#[CH:18]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C(OCC)C>[C:8]1([N:7]([CH2:18][C:17]#[CH:16])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 7842Propargyl bromideHCID 11487DiphenylamineHCID 14797Potassium Hydroxide

Product 1

HCID 10987468DIPHENYL-PROP-2-YNYL-AMINEYield 27%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a well-stirred mixture of diphenylamine (50 g, 0.3 mol), powdered potassium hydroxide (43 g, 0.65 mol) and tetrabutylammonium bromide (4.7 g, 0.015 mol) in 500 ml of tetrahydrofuran is added dropwise with cooling propargyl bromide (42 g, 0.35 mol). The resulting mixture is stirred at room temperature for one hour and then at 60° C. for ten hours. The mixture is cooled, diluted with diethyl ether and then filtered. The solvent is removed from the filtrate in vacuo to give a black oil. Distillation of said oil gives a fraction boiling at 105-107 at 0.4 torr. Said fraction is then chromatographed (silica gel, hexane) to give 16 g (27% yield) of the title compound as a pale yellow oil.

Workup

  1. waitat 60° C. for ten hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customThe solvent is removed from the filtrate in vacuo
  5. customto give a black oil
  6. distillationDistillation of said oil
  7. customgives a fraction
  8. customis then chromatographed (silica gel, hexane)

Sources & evidence

ORD record
ord-6dde85d75b2049f488bf75eebeb3cec2
Source dataset
uspto-grants-1992_09
Patent number
US05151459

Reaction notes

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