Morpholine → 4-(4-Nitrobenzyl)morpholine

HRID 1067938Notes

Reaction equation

HRID 1067938 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 7831834-(4-Nitrobenzyl)morpholine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Nitrobenzyl bromide is treated with morpholine and potassium carbonate in acetone to give 4-(4-Nitrobenzyl)morpholine (G-1). The nitro group is reduced with platinum and hydrogen gas to afford the aniline (G-2) which is then treated with [(1-ethoxycyclopropyl)-oxy]trimethylsilane and sodium cyanoborohydride to give the N-cyclopropyl aniline (G-3). Reaction with diethyl ethoxymethylenemalonate in pyridine affords the enamine (G-4) which is cyclized with polyphosphoric acid to the quinoline (G-5). Treatment with p-chlorobenzylamine at elevated temperature converts the ester to the amide (G-6).

Sources & evidence

ORD record
ord-f8c565d8f39a4968a10b45f4b719e505
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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