Acetic Acid → HCID 13288031, compound

HRID 1106057Notes

Reaction equation

HRID 1106057 reaction equation
[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:6][CH2:5][N:4]([CH3:7])[CH2:3]1.CC[O:23][CH2:24][CH3:25].[OH-].[Na+].[C:28]([OH:31])(=[O:30])[CH3:29]>B(F)(F)F.O>[C:24]([OH:23])(=[O:1])/[CH:25]=[CH:29]/[C:28]([OH:31])=[O:30].[CH3:7][N:4]1[CH2:5][CH:6]=[C:2]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:3]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 12804791HCID 12804791, compound

Product 1

HCID 13288031HCID 13288031, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6356Boron trifluorideSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 2.60 g of 3-hydroxy-1-methyl-3-(α-phenyl-2-tolyl)pyrrolidine of Example 53, in 30 ml of acetic acid and 2 ml of BF3.ether is stirred at 50°-60° C. for 21/2 hours and 16 hours at room temperature. The mixture is diluted with 30 ml of H2O, is made alkaline with NaOH, and extracted with CH2Cl2. The CH2Cl2 solution is dried (Na2SO4) and concentrated to an oil. A portion of the oil is dissolved in 10 ml of acetic acid and stirred with 0.7 ml of H2SO4 at 55° C. for 2 hours. A solution of the resultant oil in 15 ml of acetone is heated with 1.1 g of fumaric acid for dissolving and after cooling a product is isolated and recrystallized from acetone (60 ml) to provide 1-methyl-3-(α-phenyl-2-tolyl)-3 -pyrroline fumarate, mp 131°-132.5° C.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe CH2Cl2 solution is dried (Na2SO4)
  3. concentrationconcentrated to an oil
  4. dissolutionA portion of the oil is dissolved in 10 ml of acetic acid
  5. temperatureA solution of the resultant oil in 15 ml of acetone is heated with 1.1 g of fumaric acid
  6. dissolutionfor dissolving
  7. temperatureafter cooling a product
  8. customis isolated
  9. customrecrystallized from acetone (60 ml)

Sources & evidence

ORD record
ord-880ed9f5eac1468cadf3d39c425ecee2
Source dataset
uspto-grants-1982_01
Patent number
US04311703

Reaction notes

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