Morpholine → N-(3-Methoxy-4-nitro-phenyl)-N-methyl-2-morpholin-4-yl-acetamide

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]([CH3:23])[C:13](=[O:22])[CH2:14][N:15]2[CH2:20][CH2:19]N(C)[CH2:17][CH2:16]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].ClCC(N(C1C=CC([N+]([O-])=O)=C(OC)C=1)C)=[O:27].N1CCOCC1.CN1CCNCC1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]([CH3:23])[C:13](=[O:22])[CH2:14][N:15]2[CH2:20][CH2:19][O:27][CH2:17][CH2:16]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

Reactant 4

HCID 8083Morpholine

HCID 531671-Methylpiperazine

HCID 667112892-Chloro-N-(3-methoxy-4-nitro-phenyl)-N-methyl-acetamide

HCID 66712120HCID 66712120, compound

Product 1

HCID 66711708N-(3-Methoxy-4-nitro-phenyl)-N-methyl-2-morpholin-4-yl-acetamide

Procedure

N-(3-Methoxy-4-nitro-phenyl)-N-methyl-2-morpholin-4-yl-acetamide was prepared in an analogous fashion to N-(3-Methoxy-4-nitro-phenyl)-N-methyl-2-(4-methyl-piperazin-1-yl)-acetamide of Example 471a by treating the in situ generated 2-Chloro-N-(3-methoxy-4-nitro-phenyl)-N-methyl-acetamide with morpholine rather than 1-methyl piperazine. After workup the crude product was pumped under high vacuum to remove majority of morpholine, as some carried along in organic phase after extraction. Small residual amounts were separated after subsequent reduction via trituration with Et2O. (1.19 g, 73%). LC/MS (E/I+) 310.11 (M+H).