4-tert-Butylcyclohexanone → 1-[4-(Tert-butyl)-1-cyclohexen-1-YL]pyrrolidine

HRID 574135Notes

Reaction equation

HRID 574135 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C1(C)C=CC=CC=1>[C:1]([CH:5]1[CH2:10][CH2:9][C:8]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 73924-tert-ButylcyclohexanoneHCID 31268Pyrrolidine

Product 1

HCID 1072321-[4-(Tert-butyl)-1-cyclohexen-1-YL]pyrrolidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 50 mL round-bottomed flask containing 4-tert-butylcyclohexanone (6.01 gm) in anhydrous toluene (20 mL) was fitted with a Dean-Stark trap containing 3 A molecular sieves, reflux condenser and a heating mantle. Pyrrolidine (6.00 mL) was added, and the solution heated to reflux for 18 hr. The solvent was evaporated and the crude product was used directly for the next reaction.

Workup

  1. customwas fitted with a Dean-Stark trap
  2. additioncontaining 3 A molecular sieves
  3. temperaturereflux condenser
  4. temperaturethe solution heated
  5. temperatureto reflux for 18 hr
  6. customThe solvent was evaporated
  7. customthe crude product was used directly for the next reaction

Sources & evidence

ORD record
ord-1dfc076b8c0246ffa08371707ff08b15
Source dataset
uspto-grants-2015_05
Patent number
US09034871B2

Reaction notes

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