Diisopropylamine → 1-(4-Diisopropylaminomethylbenzoyl)-4-(2-naphthalenesulfonyl)piperazine

HRID 278584Notes

Reaction equation

HRID 278584 reaction equation
Cl[CH2:2][C:3]1[CH:29]=[CH:28][C:6]([C:7]([N:9]2[CH2:14][CH2:13][N:12]([S:15]([C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=3)(=[O:17])=[O:16])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH:36]([NH:39][CH:40]([CH3:42])[CH3:41])([CH3:38])[CH3:37]>CN(C=O)C>[CH:36]([N:39]([CH2:2][C:3]1[CH:29]=[CH:28][C:6]([C:7]([N:9]2[CH2:14][CH2:13][N:12]([S:15]([C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=3)(=[O:17])=[O:16])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1)[CH:40]([CH3:42])[CH3:41])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 11430Potassium CarbonateHCID 110590461-(4-Chloromethylbenzoyl)-4-(2-naphthalenesulfonyl)piperazine

Product 1

HCID 109511091-(4-Diisopropylaminomethylbenzoyl)-4-(2-naphthalenesulfonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(4-chloromethylbenzoyl)-4-(2-naphthalenesulfonyl)piperazine (300 mg), potassium carbonate (200 mg) and diisopropylamine (4 ml) in DMF (6 ml) was stirred at 100° C. for 10 hours and concentrated. To the residue was added ethyl acetate, and the mixture was washed with water, and extracted with 1 N hydrochloric acid. The extract was made alkaline with sodium hydroxide solution and extracted with dichloromethane. The extract was dried and concentrated. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2) to give the title compound (70 mg).

Workup

  1. concentrationconcentrated
  2. additionTo the residue was added ethyl acetate
  3. washthe mixture was washed with water
  4. extractionextracted with 1 N hydrochloric acid
  5. extractionextracted with dichloromethane
  6. customThe extract was dried
  7. concentrationconcentrated
  8. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-ea30e577eb3b4cd98b6b058a1effae5e
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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