2-Morpholinoethylamine → 3-(4-Nitrophenoxy)benzoic acid

HRID 78371

Reaction equation

HRID 78371 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)([OH:3])=[O:2].[NH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>>[C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1)([OH:3])=[O:2].[N:23]1([CH2:22][CH2:21][NH:20][C:1]([C:4]2[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=2)[O:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[O:3])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 7679193-(4-Nitrophenoxy)benzoic acid

Product 2

HCID 7679193-(4-Nitrophenoxy)benzoic acidHCID 66745649N-[2-(4-morpholinyl)ethyl]-3-(4-nitrophenoxy)benzamide

Procedure

Entry 61: 4-(3-Carboxyphenoxy)-1-nitrobenzene was synthesized according to Method A13, Step 2. 4-(3-Carboxyphenoxy)-1-nitrobenzene was coupled with 4-(2-aminoethyl)morpholine according to Method A13, Step 3 to give 4-(3-(N-(2-morpholinylethyl)carbamoyl)phenoxy)-1-nitrobenzene. According to Method A13 Step 4, 4-(3-(N-(2-morpholinylethyl)carbamoyl)phenoxy)-1-nitrobenzene was reduced to 4-(3-(N-(2-morpholinylethyl)carbamoyl)phenoxy)aniline. According to Method C1a, 4-chloro-3-(trifluoromethyl)phenyl isocyanate was reacted with 4-(3-(N-(2-morpholinylethyl)carbamoyl)phenoxy)aniline to afford the urea.

Sources & evidence

ORD record
ord-4b915e102afe45c180e79fc45a756656
Source dataset
uspto-grants-2014_09
Patent number
US08841330B2

Linked notes

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