Water → Phenyl{3-[1-(pyrrolidin-1-yl)prop-1-en-1-yl]phenyl}methanone

HRID 2049761Notes

Reaction equation

HRID 2049761 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.B(F)(F)F.CCO[CH2:13][CH3:14].[OH2:15].[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:22]([C:18]1[CH:17]=[C:16]([C:22]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:13][CH3:14])[CH:21]=[CH:20][CH:19]=1)(=[O:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 8000Boron trifluoride etherateHCID 31268Pyrrolidine

Product 1

HCID 54454354Phenyl{3-[1-(pyrrolidin-1-yl)prop-1-en-1-yl]phenyl}methanoneYield 41%

Procedure

In 60 ml of toluene, 1.67 g of the starting ketone, 1.49 g of pyrrolidine and 0.10 g of boron trifluoride etherate were dissolved. The mixture was refluxed for 25 hours using a Cope water separator and molecular sieve 4A as the dehydrating agent. After having distilled out the solvent, the residue was subjected to a distillation under a reduced pressure to obtain 0.83 g of the desired enamine (yield: 41%).

Workup

  1. temperatureThe mixture was refluxed for 25 hours
  2. distillationAfter having distilled out the solvent
  3. distillationthe residue was subjected to a distillation under a reduced pressure

Sources & evidence

ORD record
ord-e4fec44960a14a699014af5a58d3bca9
Source dataset
uspto-grants-1980_04
Patent number
US04198510

Reaction notes

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