Piperidine → HCID 20130461, compound

HRID 846006Notes

Reaction equation

HRID 846006 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH:8]=[CH:7][CH2:6]1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CN(C)C=O>[N:22]1([CH2:2][CH2:3][CH2:4][C:5]2([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:9][CH:8]=[CH:7][CH2:6]2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 20130467HCID 20130467, compound

Product 1

HCID 20130461HCID 20130461, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

Ethyl 1-(3-chloropropyl)-6-phenyl-3-cyclohexene-1-carboxylate (6.35 g, 20.7 mmol) was dissolved in 50 ml of dimethylformamide (DMF) to which piperidine (10 equiv, 15 ml) was added. The contents were stirred under N2 at 50° C. for 16 hrs. The reaction was allowed to cool to ambient temperature, whereupon the DMF was removed on the rotovap at 3 mm pressure. To the residue was added 200 ml of ethyl ether and the organic material was washed three times with 100 ml of water. The organic fraction was dried over MgSO4, filtered and concentrated in vacuo to afford after distillation (155°-160° C./0.1 mm) ethyl 1-[3-(1-piperidinyl)propyl]-6-phenyl-3-cyclohexene-1-carboxylate as a clear viscous oil (6.61 g, 90% yield).

Workup

  1. additionwas added
  2. customwas removed on the rotovap at 3 mm pressure
  3. additionTo the residue was added 200 ml of ethyl ether
  4. washthe organic material was washed three times with 100 ml of water
  5. dry with materialThe organic fraction was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford

Sources & evidence

ORD record
ord-54c6445a8cc24039aba467e933cb6f68
Source dataset
uspto-grants-1988_07
Patent number
US04760146

Reaction notes

Loading…