Diisopropylethylamine → HCID 19776777, compound

HRID 1612840Notes

Reaction equation

HRID 1612840 reaction equation
[CH:1]1([CH:6](Cl)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N+:31]([O-:33])=[O:32])[CH2:17][CH2:16]1.C(N(CC)C(C)C)(C)C>C(C(C)=O)C(C)C>[CH:1]1([CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:14][CH:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N+:31]([O-:33])=[O:32])[CH2:19][CH2:20]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 197767934-Hydroxy-1-[3-(2-nitrophenoxy)propyl]piperidineHCID 19776832HCID 19776832, compound

Product 1

HCID 19776777HCID 19776777, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

Into 35 ml of methyl isobutyl ketone were dissolved 2.92 g of cyclopentyl-phenylmethyl chloride, 2.80 g of 4-hydroxy-1-[3-(2-nitrophenoxy)propyl]piperidine and 1.94 g of N,N-diisopropylethylamine, and the resultant solution was heated under reflux with stirring for 72 hours. After cooling, the reaction solution was washed with water, and the solvent was removed under reduced pressure. The residue was eluted with ethyl acetate-ethanol-dichloromethane (1:1:1) by silica gel column chromatography to give 0.88 g of oily 4-(cyclopentyl-phenylmethoxy)-1-[3-(2-nitrophenoxy)propyl]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 ethyl acetate-ethanol-dichloromethane (1:1:1) by silica gel column chromatography

Sources & evidence

ORD record
ord-69f51e3892094b5eb033ea777beaccb1
Source dataset
uspto-grants-1993_03
Patent number
US05190959

Reaction notes

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