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

HRID 1262053Notes

Reaction equation

HRID 1262053 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

5

Reactant 4

HCID 8083MorpholineHCID 531671-MethylpiperazineHCID 667112892-Chloro-N-(3-methoxy-4-nitro-phenyl)-N-methyl-acetamideHCID 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).

Workup

  1. additionby treating the in situ
  2. customto remove majority of morpholine
  3. extractionafter extraction
  4. customSmall residual amounts were separated after subsequent reduction via trituration with Et2O

Sources & evidence

ORD record
ord-629466b5dd2d44029e78522caaa9f4c7
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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