Toluene → HCID 19776774, compound

HRID 1612833Notes

Reaction equation

HRID 1612833 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[O:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.Cl[CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[N+:40]([O-:42])=[O:41]>C(N(CC)CC)C>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[O:16][CH:17]1[CH2:18][CH2:19][N:20]([CH2:30][CH2:31][CH2:32][O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[N+:40]([O-:42])=[O:41])[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 10335053HCID 10335053, compoundHCID 114244631-(3-Chloro-propoxy)-2-nitro-benzene

Product 1

HCID 19776774HCID 19776774, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into 50 ml of toluene were dissolved 3.02 g of 4-[(2-chlorophenyl)-phenylmethoxy]piperidine, 2.59 g of 1-chloro-3-(2-nitrophenoxy)propane and 3.04 g of triethylamine, and the resultant solution was heated under reflux with stirring for 15 hours. After cooling, the reaction solution was washed with water, and the solvent was removed under reduced pressure. The residue was eluted with methanol-chloroform (1:50) by silica gel column chromatography to give 3.55 g of oily 4-[(2-chlorophenyl)-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 methanol-chloroform (1:50) by silica gel column chromatography

Sources & evidence

ORD record
ord-bd0c2381d0d349f5a3e6b48a4f83652e
Source dataset
uspto-grants-1993_03
Patent number
US05190959

Reaction notes

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