Pyrrolidine → HCID 178484904, compound

HRID 1492248Notes

Reaction equation

HRID 1492248 reaction equation
I.CS[C:4](=[N:18][CH3:19])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>C(O)C>[CH3:19][NH:18][C:4]([N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)=[N:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 18952225HCID 18952225, compound

Product 1

HCID 178484904HCID 178484904, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-methyl-1-(2-morpholinophenyl)-3-methyl-2-thiopseudourea hydriodide (3.9 g prepared as described in Example 210), pyrrolidine (1 ml) and ethanol (40 ml) was heated under reflux for two weeks to yield an oil which was purified by chromatography on a neutra alumina column eluted with a 1:1 mixture of dichloromethane and hexane and then a 1:9 mixture of methanol and dichloromethane to give N-methyl-N'-(2-morpholinophenyl)pyrrolidine-1-carboxamidine which was converted into its monofumarate salt (m.p. 168°-171° C.) which was recrystallised from propan-2ol.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for two weeks
  3. customto yield an oil which
  4. customwas purified by chromatography on a neutra alumina column
  5. washeluted with a 1:1 mixture of dichloromethane and hexane
  6. additiona 1:9 mixture of methanol and dichloromethane

Sources & evidence

ORD record
ord-8cb6600474ca4da187644697cff57de9
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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