Triprolidine → 1-(4-Methylphenyl)-1-(2-pyridyl)-3-pyrrolidino prop-1-ene

HRID 1803092Notes

Reaction equation

HRID 1803092 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5](/[C:8](/[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][N:21]=2)=[CH:9]\[CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:6][CH:7]=1>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][N:21]=2)=[CH:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 5282443Triprolidine

Product 1

HCID 55881-(4-Methylphenyl)-1-(2-pyridyl)-3-pyrrolidino prop-1-eneYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60 ml of demineralized water is charged into a round-bottomed flask kept at 25° to 30° C. and then slowly 540 ml of 90% Conc. H2SO4 is added and the temperature is raised to 40° C.-60° C. under stirring. Slowly 200 g of 1-(4-methylphenyl)-1-(2-pyridyl)-3-pyrrolidinopropan-1-ol is charged and the temperature is maintained at 85° C. under stirring. The reaction mass is heated to 100-105° C. and the temperature is maintained for 4 hours under stirring. After completion of the reaction, the reaction mass is cooled to 25°-30° C. and then poured into ice cold water (4 litre) at 5-10° C. under stirring over a period of an hour. 50% NaOH solution (w/w) is added slowly to the reaction mixture by maintaining the temperature at 5° to 20° C. over a period of 2 hours and the contents are stirred for an hour at 25° to 30° C. The reaction mixture is filtered under suction to obtain 286 g of wet triprolidine base comprising >92% E-isomer along with <8% Z-isomer. 2 litres of demineralized water and 286 g of wet triprolidine base are charged into a round-bottom flask at 25° to 30° C. and the contents are stirred for 3 hours by maintaining the same temperature. The contents are filtered and dried under suction for 2 hours. The process is repeated thrice to obtain 1-(4-methylphenyl)-1-(2-pyridyl)-3-pyrrolidino prop-1-ene (150 g, 80%) consisting of >98% E isomer along with <2% Z-isomer.

Workup

  1. temperatureby maintaining the same temperature
  2. filtrationThe contents are filtered
  3. customdried under suction for 2 hours

Sources & evidence

ORD record
ord-ffdab0bcc1be4cb28e12e566f8d5e848
Source dataset
uspto-grants-2013_01
Patent number
US08350045B2

Reaction notes

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