Dichloromethane → HCID 12804797, compound

HRID 1648920Notes

Reaction equation

HRID 1648920 reaction equation
C(O)(=O)C(O)=O.C(O[C:11]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14][N:13](CC2C=CC=CC=2)[CH2:12]1)(=O)C.[OH-].[Na+].C(Cl)[Cl:39]>>[ClH:39].[C:30]1([CH2:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH:11]2[CH2:15][CH2:14][NH:13][CH2:12]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 12804795HCID 12804795, compound

Product 1

HCID 12804797HCID 12804797, compound

Procedure

25.9 g of 3-acetoxy-1-benzyl-3-(α-phenyl-2-tolyl)pyrrolidine oxalate of Example 57 is suspended at 0° C. in 500 ml CH2Cl2 and stirred with a slight excess of 5% NaOH for 1/2 hour. The organic layer is washed with water, dried (Na2SO4), and concentrated to an oil. This oil is dissolved in 200 ml of i-propanol and the solution is made acidic with a very slight excess of HCl/i-propanol and hydrogenated with 5 g of Pd on carbon (10%) at 70° C. and 60 psig for 8 hours. After filtration the solution is diluted with 700 ml of ether and after cooling the product is collected by filtration. Recrystallization from methanol-ether (40 ml-160 ml) provides 3-(α-phenyl-2-tolyl)pyrrolidine hydrochloride, mp 148°-149° C.

Workup

  1. washThe organic layer is washed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated to an oil
  4. dissolutionThis oil is dissolved in 200 ml of i-propanol
  5. filtrationAfter filtration the solution
  6. additionis diluted with 700 ml of ether
  7. temperatureafter cooling the product
  8. filtrationis collected by filtration
  9. customRecrystallization from methanol-ether (40 ml-160 ml)

Sources & evidence

ORD record
ord-8648530c92ab46a9ab7d95b1b16e3cba
Source dataset
uspto-grants-1983_11
Patent number
US04414219

Reaction notes

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