Diisopropylethylamine → 4-(phenyl-2-thienylmethoxy)-1-[4-(2-nitrophenoxy)-2(E)-butenyl]piperidine

HRID 1612848Notes

Reaction equation

HRID 1612848 reaction equation
[C:1]1([CH:7](Cl)[C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21]/[CH:22]=[CH:23]/[CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])[CH2:17][CH2:16]1.C(N(CC)C(C)C)(C)C>C(C(C)=O)C(C)C>[C:1]1([CH:7]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[O:14][CH:15]2[CH2:16][CH2:17][N:18]([CH2:21]/[CH:22]=[CH:23]/[CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N+:32]([O-:34])=[O:33])[CH2:19][CH2:20]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10512583Phenyl-2-thienylmethyl chlorideHCID 197767194-hydroxy-1-[4-(2-nitrophenoxy)-2(E)-butenyl]piperidine

Product 1

HCID 197767104-(phenyl-2-thienylmethoxy)-1-[4-(2-nitrophenoxy)-2(E)-butenyl]piperidineYield 65.8%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

Into 20 ml of methyl isobutyl ketone were dissolved 2.09 g of phenyl-2-thienylmethyl chloride, 3.50 g of 4-hydroxy-1-[4-(2-nitrophenoxy)-2(E)-butenyl]piperidine and 1.94 g of N,N-diisopropylethylamine, and the resultant solution was heated under reflux with stirring for 2 hours. After cooling, the reaction solution was washed with water, and the solvent was removed under reduced pressure. The residue was eluted with ethanol-chloroform (1:50) by silica gel column chromatography to give 3.06 g of oily 4-(phenyl-2-thienylmethoxy)-1-[4-(2-nitrophenoxy)-2(E)-butenyl]piperidine.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. washthe reaction solution was washed with water
  4. customthe solvent was removed under reduced pressure
  5. washThe residue was eluted with ethanol-chloroform (1:50) by silica gel column chromatography

Sources & evidence

ORD record
ord-b8355699bb7b40c680a8e16e51f6c62b
Source dataset
uspto-grants-1993_03
Patent number
US05190959

Reaction notes

Loading…