p-Fluoronitrobenzene → 4-(4-Aminophenyl)morpholine-3-carboxylic acid ethyl ester

HRID 905666Notes

Reaction equation

HRID 905666 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][CH:3]=1.[CH2:11]([O:13][C:14]([CH:16]1[CH2:21][O:20][CH2:19][CH2:18][NH:17]1)=[O:15])[CH3:12].C(N(C(C)C)CC)(C)C>CS(C)=O>[CH2:11]([O:13][C:14]([CH:16]1[CH2:21][O:20][CH2:19][CH2:18][N:17]1[C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1)=[O:15])[CH3:12]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 18354446Ethyl morpholine-3-carboxylate

Product 1

HCID 673886544-(4-Aminophenyl)morpholine-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Fluoronitrobenzene and morpholine-3-carboxylic acid ethyl ester were allowed to undergo the reaction at 100° C. in DMSO in the presence of diisopropylethylamine, and then the resulting compound was subjected to catalytic hydrogenation in the same manner as shown in Reference Example 3 to obtain 4-(4-aminophenyl)morpholine-3-carboxylic acid ethyl ester. ESI: 251.

Sources & evidence

ORD record
ord-298e399cb0d04c3196e0290bcb040c7f
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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