Pyrrolidine → 1-(4-PHENYLCYCLOHEX-1-ENYL)PYRROLIDINE

HRID 2188408Notes

Reaction equation

HRID 2188408 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]1([CH:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CCCCCC.[Ti](Cl)(Cl)(Cl)Cl>[C:6]1([CH:12]2[CH2:17][CH2:16][C:15]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 786054-Phenylcyclohexanone

Product 1

HCID 122646591-(4-PHENYLCYCLOHEX-1-ENYL)PYRROLIDINEYield 51.7%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalyst2×HCID 8058HexaneSolvent5×

Conditions

Temperature
0 °C

Procedure

36.8 g (0.517 mole) of pyrrolidine dissolved in 170 ml of n-hexane were added dropwise to 30.0 g (0.172 mole) of 4-phenylcyclohexanone dissolved in 860 ml of n-hexane, and the solution was cooled to 0° C. in an ice bath. 18.0 g (0.095 mole) of titanium tetrachloride dissolved in 140 ml of n-hexane were added dropwise within one hour at 0° C.-10° C., stirred for a further two hours at RT, following which the suspension was filtered. The filtrate was concentrated by evaporation on a rotary evaporator (500 to 10 mbar), and the remaining oil was purified by distillation at a pressure of less than 1 mbar; the main fraction boiled at 135° C. 22.2 of crude product were obtained, which on account of incomplete conversion underwent, in the cold, the addition of 27.2 g (0.379 mole) of pyyrolidine dissolved in 125 ml of n-hexane and 13.1 g (0.069 mole) of titanium tetrachloride dissolved in 140 ml of n-hexane, and the mixture was then heated under reflux for two hours. 20.2 g of 1-(4-phenylcyclohex-1-enyl)pyrrolidine (51.7% of theory) were obtained in this way.

Workup

  1. additionwere added dropwise within one hour at 0° C.-10° C.
  2. filtrationwas filtered
  3. concentrationThe filtrate was concentrated by evaporation on a rotary evaporator (500 to 10 mbar)
  4. distillationthe remaining oil was purified by distillation at a pressure of less than 1 mbar
  5. custom22.2 of crude product were obtained
  6. additionwhich on account of incomplete conversion underwent, in the cold, the addition of 27.2 g (0.379 mole) of pyyrolidine
  7. temperaturethe mixture was then heated
  8. temperatureunder reflux for two hours

Sources & evidence

ORD record
ord-c5c875b19a5148fe8d8fcbf6b2f3090e
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

Loading…