Triethylamine → 1-[4-(1-Acetimidoylpiperidin-4-yl)benzoyl]-4-(6-chloronaphthalene-2-sulfonyl)piperazine hydrochloride

HRID 278608Notes

Reaction equation

HRID 278608 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:35]=[CH:34][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([S:20]([C:23]4[CH:32]=[CH:31][C:30]5[C:25](=[CH:26][CH:27]=[C:28]([Cl:33])[CH:29]=5)[CH:24]=4)(=[O:22])=[O:21])[CH2:16][CH2:15]3)=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[CH2:36]([N:38](CC)CC)[CH3:37].Cl.C(=N)(OCC)C>CO>[ClH:33].[C:36]([N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:35]=[CH:34][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([S:20]([C:23]4[CH:32]=[CH:31][C:30]5[C:25](=[CH:26][CH:27]=[C:28]([Cl:33])[CH:29]=5)[CH:24]=4)(=[O:22])=[O:21])[CH2:16][CH2:15]3)=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1)(=[NH:38])[CH3:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 227110601-(6-Chloronaphthalene-2-sulfonyl)-4-[4-(4-piperidyl)benzoyl]piperazine hydrochloride

Product 1

HCID 226280911-[4-(1-Acetimidoylpiperidin-4-yl)benzoyl]-4-(6-chloronaphthalene-2-sulfonyl)piperazine hydrochlorideYield 195%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[4-(piperidin-4-yl)benzoyl]-4-(6-chloronaphthalene-2-sulfonyl)piperazine hydrochloride (40 mg) and triethylamine (156 mg) in methanol (15 ml) was added ethyl acetimidate hydrochloride (46 mg), and the solution was stirred at room temperature for 15 hours. The reaction solution was concentrated. To the residue was added 1 N sodium hydroxide solution, and the solution was extracted with dichloromethane. The extract was dried and concentrated. The residue was dissolved in ethyl acetate, to which was added 4 N hydrochloric acid in ethyl acetate. The precipitate was filtered, washed with ether and dried to give a colorless solid of the title compound (42 mg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionTo the residue was added 1 N sodium hydroxide solution
  3. extractionthe solution was extracted with dichloromethane
  4. customThe extract was dried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ethyl acetate, to which
  7. additionwas added 4 N hydrochloric acid in ethyl acetate
  8. filtrationThe precipitate was filtered
  9. washwashed with ether
  10. customdried

Sources & evidence

ORD record
ord-13a54221185a48bfbe3cbef54115fb73
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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