Pyrrolidine → HCID 178506599, compound

HRID 866859Notes

Reaction equation

HRID 866859 reaction equation
[IH:1].[Cl: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].[Cl: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 178504034HCID 178504034, compound

Product 1

HCID 178506599HCID 178506599, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 7.0 g (0.017 mole) of methyl N-(4-chlorobenzhydryl)carbamimidothioate hydroiodide and 2.85 g (0.04 mole) of pyrrolidine in 20 mls of t-BuOH is heated at reflux overnight. The t-BuOH is removed in vacuo and the crude guanidine hydroiodide is crystallized from methanol-ether. The crude product is recrystallized from methanol-t-butanol to yield pure N-(4-chlorobenzhydryl)-1-pyrrolidinecarboximidamide hydroiodide; mp 218°-220° (dec).

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. customThe t-BuOH is removed in vacuo
  4. customthe crude guanidine hydroiodide is crystallized from methanol-ether
  5. customThe crude product is recrystallized from methanol-t-butanol

Sources & evidence

ORD record
ord-225a5d08e14f419c8dc486594e2658c3
Source dataset
uspto-grants-1978_07
Patent number
US04101659

Reaction notes

Loading…