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

HRID 1656367Notes

Reaction equation

HRID 1656367 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-460d7d25443a44b684552ed4c766007d
Source dataset
uspto-grants-1993_10
Patent number
US05254552

Reaction notes

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