Potassium Carbonate → 4-Morpholin-4-yl-3-(2-morpholin-4-ylethoxy)aniline hydrochloride

HRID 269819Notes

Reaction equation

HRID 269819 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=2[OH:16])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+].Cl.C(OCC)(=O)C>CN(C=O)C.C(OCC)(=O)C>[ClH:17].[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=2[O:16][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 767274-(2-Chloroethyl)morpholineHCID 21866389Hydrogen chloride-ethyl acetateHCID 230715652-Morpholin-4-yl-5-nitrophenol

Product 1

HCID 692792464-Morpholin-4-yl-3-(2-morpholin-4-ylethoxy)aniline hydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Morpholin-4-yl-5-nitrophenol and 4-(2-chloroethyl)morpholine were allowed to undergo the reaction in DMF in the presence of potassium carbonate, and then the resulting compound was subjected to catalytic hydrogenation in the same manner as shown in Reference Example 3 and further treated with 4 M hydrogen chloride/ethyl acetate solution in ethyl acetate to obtain 4-morpholin-4-yl-3-(2-morpholin-4-ylethoxy)aniline hydrochloride F: 308.

Sources & evidence

ORD record
ord-31fe0aac4ff8425bbede4e7b2058b20f
Source dataset
uspto-grants-2008_11
Patent number
US07449456B2

Reaction notes

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