Triethylamine → N-[2-[4-(2-Pyrimidinyl)-1-piperazinyl]ethyl]-2-benzofurancarboxamide Dihydrochloride Hydrate

HRID 1768968Notes

Reaction equation

HRID 1768968 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH2:15])[CH2:9][CH2:8]1.[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[C:25]([Cl:27])=[O:26].C(N(CC)CC)C>C(Cl)Cl>[OH2:16].[ClH:27].[ClH:27].[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH:15][C:25]([C:17]2[O:16][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH:18]=2)=[O:26])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 389492-Benzofurancarbonyl chlorideHCID 138853581-Piperazineethanamine, 4-(2-pyrimidinyl)-

Product 1

HCID 18995774N-[2-[4-(2-Pyrimidinyl)-1-piperazinyl]ethyl]-2-benzofurancarboxamide Dihydrochloride Hydrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [4-(2-pyrimidinyl)piperazino]ethylamine (2.0 g, 0.01 mol) in 50 mL of methylene chloride, benzofurane-2-carboxylic acid chloride (2.6 g, 0.014 mol) and triethylamine (2 g, 0.02 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. The title compound was separated and converted to the dihydrochloride hydrate salt with ethanolic HCl (0.5 g), m.p. 193° 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-bf57c54cb1e34a93af187824ee8d29e2
Source dataset
uspto-grants-1995_01
Patent number
US05380725

Reaction notes

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