Triethylamine → N-[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]-2-benzofurancarboxamide Dihydrochloride

HRID 1197832Notes

Reaction equation

HRID 1197832 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10]1.[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH:21]=[C:20]1[C:28]([Cl:30])=[O:29].C(N(CC)CC)C>C(Cl)Cl>[ClH:30].[ClH:30].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:28]([C:20]2[O:19][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH:21]=2)=[O:29])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 389492-Benzofurancarbonyl chlorideHCID 104672591-(3-Aminopropyl)-4-(2-methoxyphenyl)piperazine

Product 1

HCID 18995783N-[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]-2-benzofurancarboxamide Dihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [4-(2-methoxyphenyl)piperazinyl]propylamine (1.0 g, 0.04 mol) in 50 mL of methylene dichloride, benzofurane-2-carboxylic acid chloride (1.01 g, 0.0056 mol) and triethylamine (1 g, 0.01 mol) were added. Stirring was continued at room temperature overnight. The methylene chloride solution was washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The remaining residue was subjected to preparative HPLC using silica gel column and ethyl acetate as the eluent. The title compound was separated and converted to the dihydrochloride salt with ethanolic HCl (0.9 g), m.p. 228°-232° C.

Workup

  1. washThe methylene chloride solution was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated under reduced pressure
  4. customThe title compound was separated

Sources & evidence

ORD record
ord-cc7251e58283440882861211d5286401
Source dataset
uspto-grants-1994_01
Patent number
US05278160

Reaction notes

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