Pyrrolidine → HCID 178425552, compound

HRID 866863Notes

Reaction equation

HRID 866863 reaction equation
[IH:1].[CH3:2][C:3]1[CH:20]=[CH:19][C:6]([CH:7]([NH:14][C:15](SC)=[NH:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>CC(O)(C)C>[IH:1].[CH3:2][C:3]1[CH:20]=[CH:19][C:6]([CH:7]([NH:14][C:15]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[NH:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 178504032HCID 178504032, compound

Product 1

HCID 178425552HCID 178425552, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 13.3 g (0.0334 mole) of methyl N-(4-methylbenzhydryl)carbamimidothioate hydroiodide and 5.0 g (0.07 mole) of pyrrolidine in 40 mls of t-BuOH is heated under reflux for 24 hrs. The crude product crystallizes out of the reaction mixture while refluxing. The mixture is allowed to cool over night at room temperature and filtered to yield crude product; mp 227°-30° C. Recrystallization from MeOH/t-BuOH yields the pure N-(4-methylbenzhydryl)-1-pyrrolidinecarboximidamide hydroiodide; mp 229°-230° C, as a white solid.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 24 hrs
  3. customThe crude product crystallizes out of the reaction mixture
  4. temperaturewhile refluxing
  5. filtrationfiltered
  6. customto yield crude product
  7. customRecrystallization from MeOH/t-BuOH

Sources & evidence

ORD record
ord-f8fb022e66914754bfdaed45c78befa2
Source dataset
uspto-grants-1978_07
Patent number
US04101659

Reaction notes

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