p-Fluoronitrobenzene → HCID 6930630, compound

HRID 269803Notes

Reaction equation

HRID 269803 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][CH:3]=1.[CH3:11][CH:12]1[O:17][CH:16]([CH3:18])[CH2:15][NH:14][CH2:13]1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:18][C@H:16]1[O:17][C@@H:12]([CH3:11])[CH2:13][N:14]([C:2]2[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=2)[CH2:15]1.[CH3:18][C@H:16]1[O:17][C@H:12]([CH3:11])[CH2:13][N:14]([C:2]2[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=2)[CH2:15]1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 1108622,6-Dimethylmorpholine

Product 2

HCID 6930630HCID 6930630, compoundHCID 6930633HCID 6930633, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Fluoronitrobenzene and 2,6-dimethylmorpholine were allowed to undergo the reaction in DMF in the presence of diisopropylethylamine, and then cis and trans isomers were separated and purified by a silica gel column chromatography and respectively subjected to catalytic hydrogenation in the same manner as shown in Reference Example 3 to obtain cis-4-(2,6-dimethylmorpholin-4-yl)aniline (Reference Example 7; F: 207) and trans-4-(2,6-dimethylmorpholin-4-yl)aniline (Reference Example 8; F: 207).

Workup

  1. customcis and trans isomers were separated
  2. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-d1bc2db958bf476f9f242c8427ea0c36
Source dataset
uspto-grants-2008_11
Patent number
US07449456B2

Reaction notes

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