4-Methylpiperidine → HCID 68818181, compound

HRID 1820855Notes

Reaction equation

HRID 1820855 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[Cl:14].[CH3:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>C(Cl)Cl>[Cl:14][C:6]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH2:2][N:19]1[CH2:20][CH2:21][CH:16]([CH3:15])[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 693814-MethylpiperidineHCID 3099731-(2-bromoethoxy)-2-chloro-4-nitrobenzene

Product 1

HCID 68818181HCID 68818181, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.80 g (27.8 mmol) of 4-(2-bromoethoxy)-3-chloronitrobenzene (III.1.a) and 10.1 mL (84.0 mmol) of 4-methylpiperidine is dissolved in 100 mL of methylene chloride and stirred for 12 hours at ambient temperature. Then the mixture is filtered through 400 g of aluminum oxide (activity 2-3) with methylene chloride/methanol 49:1 as eluant. Yield: 6.9 g (83% of theory); Rf value: 0.50 (aluminum oxide, petroleum ether/ethyl acetate=3:1); C14H19ClN2O3; EII mass spectrum: m/z=299/301 [M+H]+.

Workup

  1. filtrationThen the mixture is filtered through 400 g of aluminum oxide (activity 2-3) with methylene chloride/methanol 49:1 as eluant

Sources & evidence

ORD record
ord-898cacba1a264b0bbf1508bf5d477a7b
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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