2-Methoxy-1-Pyrroline → HCID 46834862, compound

HRID 1928699Notes

Reaction equation

HRID 1928699 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([NH2:17])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.CO[C:20]1[CH2:21][CH2:22][CH2:23][N:24]=1>CO.C(O)(=O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([NH:17][C:20]1[CH2:21][CH2:22][CH2:23][N:24]=1)[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 3534432-Methoxy-1-PyrrolineHCID 59365474HCID 59365474, compound

Product 1

HCID 46834862HCID 46834862, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To 1-(2,3-dichlorophenyl)-2-(pyridin-3-yl)ethanamine (258 mg, 0.97 mmol) in methanol (5 mL) was added 5-methoxy-3,4-dihydro-2H-pyrrole (96 mg, 0.97 mmol) followed by acetic acid (2 drops). The mixture was heated at 70° C. for 16 hours. The mixture was cooled to room temperature and methanol was removed. Purification by chromatography on silica gel (5% 7N NH3 in MeOH/CH2Cl2) gave N-(1-(2,3-dichlorophenyl)-2-(pyridin-3-yl)ethyl)-3,4-dihydro-2H-pyrrol-5-amine (161 mg, 50%) as an off white solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custommethanol was removed
  3. customPurification by chromatography on silica gel (5% 7N NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-087e93836af24d9fb06eee80f36ce8f8
Source dataset
uspto-grants-2012_05
Patent number
US08183414B2

Reaction notes

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