Triethylamine → N-(1-Methyl-2-pyrrolidinylidene)-N'-phenyl-1-pyrrolidinecarboximidamide

HRID 2057627Notes

Reaction equation

HRID 2057627 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([N:7]=[C:8](Cl)Cl)=[CH:3][CH:2]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.CCN(CC)CC.[CH3:23][N:24]1[CH2:28][CH2:27][CH2:26][C:25]1=[NH:29].[C:30]([OH:39])(=[O:38])[C@@H:31]([C@H:33]([C:35]([OH:37])=[O:36])[OH:34])[OH:32]>CCOCC.CO>[C:35]([C@@H:33]([C@H:31]([C:30]([O-:39])=[O:38])[OH:32])[OH:34])([O-:37])=[O:36].[CH3:23][N:24]1[CH2:28][CH2:27][CH2:26][C:25]1=[N:29][C:8]([N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[N:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 12145Phenylimidocarbonyl chlorideHCID 31268PyrrolidineHCID 444305L-Tartaric acidHCID 124489661-Methyl-2-pyrrolidinimine

Product 2

HCID 44104N-(1-Methyl-2-pyrrolidinylidene)-N'-phenyl-1-pyrrolidinecarboximidamideHCID 119400Tartrate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To 1.74 g (0.01 mole) of phenyl isocyanide dichloride in dry Et2O with cooling under N2 is added 0.71 g (0.01 mole) of pyrrolidine followed by 1.01 g (0.01 mole) of Et3N with stirring. The mixture is allowed to stir for 11/2 hrs. and then filtered to remove precipitated Et3N.HCl. To the filtrate is added 1.96 g (0.02 mole) of 1-methyl-2-iminopyrrolidine in an ice-water bath. The resultant mixture is allowed to stir overnight under N2 and then filtered to remove N-methyl-2-iminopyrrolidine hydrochloride, m.p. 182°-188° C. The filtrate is evaporated to dryness in vacuo affording in an oil which is dissolved in MeOH (10 ml) and treated with an equimolar amount of L(+)-tartaric acid. The resultant solution is concentrated while adding i-PrOH to give crystals. Recrystallization from isopropanol-acetonitrile gives the pure L-(+)-tartrate salt, N-(1-methyl-2-pyrrolidinylidene)-N'-phenyl-1-pyrrolidinecarboximidamide, m.p. 153°-56° C.

Workup

  1. stirringto stir for 11/2 hrs
  2. filtrationand then filtered
  3. customto remove
  4. customprecipitated Et3N.HCl
  5. stirringto stir overnight under N2
  6. filtrationfiltered
  7. customto remove N-methyl-2-iminopyrrolidine hydrochloride, m.p. 182°-188° C
  8. customThe filtrate is evaporated to dryness in vacuo
  9. customaffording in an oil which
  10. concentrationThe resultant solution is concentrated
  11. additionwhile adding i-PrOH
  12. customto give crystals
  13. customRecrystallization from isopropanol-acetonitrile

Sources & evidence

ORD record
ord-bfff5bde7d7541a883b6bfa7fa7ddf7e
Source dataset
uspto-grants-1980_07
Patent number
US04211867

Reaction notes

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