Morpholine → HCID 22291049, compound

HRID 1369552Notes

Reaction equation

HRID 1369552 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:33]([O-:35])=[O:34])=[C:6]([CH:32]=1)[C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:31])=[C:14]([NH:16][C:17](=[O:30])[C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:20][CH:19]=2)[CH:15]=1)=[O:8].[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>C(Cl)Cl>[CH3:31][C:13]1[CH:12]=[CH:11][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:32]=[C:2]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[CH:3]=[CH:4][C:5]=2[N+:33]([O-:35])=[O:34])=[CH:15][C:14]=1[NH:16][C:17](=[O:30])[C:18]1[CH:19]=[CH:20][C:21]([CH2:24][N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 22291124HCID 22291124, compound

Product 1

HCID 22291049HCID 22291049, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Using an analogous procedure to that described in Example 67 except that the reaction mixture was heated to 105° C. for 16 hours rather than to 100° C. for 6 days, N-[5-(5-chloro-2-nitrobenzamido)-2-methylphenyl]-4-diethylaminomethylbenzamide was reacted with morpholine. The solid so obtained was dissolved in methylene chloride and the solution was washed with a saturated aqueous sodium bicarbonate solution. The organic solution was dried (MgSO4) and evaporated. There was thus obtained the title compound in 64% yield; NMR Spectrum: (DMSOd6) 0.98 (t, 6H), 2.2 (s, 3H), 2.4-2.6 (m, 4H), 3.4-3.5 (m, 4H), 3.6 (s, 2H), 3.7-3.8 (m, 4H), 7.0-7.1 (m, 2H), 7.2 (m, 1H), 7.4-7.5 (m, 2H), 7.7 (m, 1H), 7.9 (d, 2H), 8.05 (d, 1H), 9.85 (s, 1H), 10.38 (broad s, 1H); Mass Spectrum: M+H+546.

Workup

  1. customThe solid so obtained
  2. washthe solution was washed with a saturated aqueous sodium bicarbonate solution
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-04e14f6b182e4b128b9610a08a1cd15a
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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