Pyrrolidine → HCID 20138891, compound

HRID 280150Notes

Reaction equation

HRID 280150 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=O.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]=[C:8]2[N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 366205-Methoxytetralone

Product 1

HCID 20138891HCID 20138891, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent2×

Procedure

Titanium tetrachloride (31.1 ml) in dry toluene (210 ml) is added slowly to a stirred solution of 5-methoxy-1-tetralone (100 g) and pyrrolidine (263 g) in anhydrous toluene (2 l) cooled in a methanol ice bath under N2 while maintaining a temperature of less than 7° C. When the addition is complete, the reaction mixture is allowed to stir at RT for 31/2 hrs. The reaction mixture is filtered, the solid washed with anhydrous toluene, and the filtrate evaporated in vacuo, resulting in a gold viscous liquid, which is dissolved in 1.8 l of dry tetrahydrofuran and filtered. The filtrate is used as is in the next step.

Workup

  1. temperaturecooled in a methanol ice bath under N2
  2. temperaturewhile maintaining a temperature of less than 7° C
  3. additionWhen the addition
  4. filtrationThe reaction mixture is filtered
  5. washthe solid washed with anhydrous toluene
  6. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-98a04aaaf6dc47ad89157c446552902a
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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