Triethylamine → (4-(2-Chlorophenyl)piperazin-1-yl)(2-morpholino-5-nitrophenyl)methanone

HRID 736125

Reaction equation

HRID 736125 reaction equation
[N:1]1([C:7]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=2[C:9](Cl)=[O:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.CCN(CC)CC>C(Cl)Cl>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][N:29]([C:9]([C:8]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:7]=2[N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:10])[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4156281-(2-Chlorophenyl)piperazineHCID 172741532-Morpholin-4-yl-5-nitro-benzoyl chloride

Product 1

HCID 44580055(4-(2-Chlorophenyl)piperazin-1-yl)(2-morpholino-5-nitrophenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 18.9 mg (0.07 mmol) 2-Morpholin-4-yl-5-nitro-benzoyl chloride, 16.5 mg (0.084 mmol) 1-(2-Chloro-phenyl)-piperazine and 34 ul (0.245 mmol) NEt3 in 2 ml DCM was stirred at room temperature for 16 h. After evaporation of the volatiles the residue was taken up in 2 ml CH3CN/MeOH/HCOOH 2/2/1 and subjected to preparative HPLC purification on reversed phase eluting with an acetonitrile/water gradient to yield after evaporation of the product fractions 23.2 mg (77%) of the title compound.

Workup

  1. customAfter evaporation of the volatiles the residue
  2. customsubjected to preparative HPLC purification on reversed phase
  3. washeluting with an acetonitrile/water gradient
  4. customto yield
  5. customafter evaporation of the product fractions 23.2 mg (77%) of the title compound

Sources & evidence

ORD record
ord-e03af22e8e014088bb06608bdf9e919c
Source dataset
uspto-grants-2009_09
Patent number
US07595314B2

Linked notes

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