Potassium Carbonate → 4-(3-Nitro-4-piperidin-1-yl-phenyl)-morpholine

HRID 646853Notes

Reaction equation

HRID 646853 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:16])[CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)([O-:3])=[O:2].Br[CH2:18][CH2:19][O:20][CH2:21][CH2:22]Br.C([O-])([O-])=O.[K+].[K+].CCOCC.CCCCCC>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([N:16]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:7]=[CH:8][C:9]=1[N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 27602373-Nitro-4-(piperidin-1-yl)anilineHCID 21584099Diethylether hexane

Product 1

HCID 586385494-(3-Nitro-4-piperidin-1-yl-phenyl)-morpholineYield 70.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure of Example 10, step (b) using 152 mg (0.687 mmol) of 3-nitro-4-piperidin-1-yl-phenylamine (as prepared in Example 10, step (a)), 78.6 mg (0.625 mmol) of 2-bromoethyl ether and 433 mg (3.13 mmol) of anh K2CO3 except the mixture was heated to reflux in 2 mL of toluene for 20 h. Chromatography on a 10-g silica SPE column with 40% Et2O-hexane afforded 128 mg (70%) of the title compound as a dark orange resin: Mass spectrum (ESI, m/z): Calcd. for C15H21N3O2, 292.2 (M+H), found 292.1.

Workup

  1. customThe title compound was prepared
  2. temperaturewas heated

Sources & evidence

ORD record
ord-ee4460e9c8754de798f9f1b614202f23
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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