1-(1-Naphthyl)piperazine → 6-(2-(4-(1-Naphthyl)-piperazinyl)ethyl)benzothiazolone

HRID 1935389Notes

Reaction equation

HRID 1935389 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[CH:9][S:10](=[O:11])[C:6]=2[CH:5]=1.[C:14]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(CC(C)C)=O>[C:14]1([N:24]2[CH2:29][CH2:28][N:27]([CH2:2][CH2:3][C:4]3[CH:13]=[CH:12][C:7]4[N:8]=[CH:9][S:10](=[O:11])[C:6]=4[CH:5]=3)[CH2:26][CH2:25]2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 13421-(1-Naphthyl)piperazineHCID 10340Sodium CarbonateHCID 692279736-(2-Bromoethyl)benzothiazolone

Product 1

HCID 692310686-(2-(4-(1-Naphthyl)-piperazinyl)ethyl)benzothiazolone

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 100 ml round-bottomed flask with condenser and nitrogen inlet were added 1.0 gram (3.88 mmol) of 6-(2-bromoethyl)benzothiazolone, 822 mg (3.88 mmol) N-(1-naphthyl)piperazine, 410 mg (3.88 mmol) sodium carbonate, and 50 ml methylisobutlyketone. The reaction was refluxed for 24 hours, cooled, and evaporated. The residue was taken up in ethyl acetate, washed with water and brine, dried over sodium sulfate, and evaporated. The resulting solid was treated with hot ethyl acetate to afford a white solid, m.p. 198°-220° C., 540 mg (36%).

Workup

  1. temperatureThe reaction was refluxed for 24 hours
  2. temperaturecooled
  3. customevaporated
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. additionThe resulting solid was treated with hot ethyl acetate
  8. customto afford a white solid, m.p. 198°-220° C., 540 mg (36%)

Sources & evidence

ORD record
ord-23c24dd3c50e4fd5915305497a543a90
Source dataset
uspto-grants-2002_05
Patent number
US06387904B2

Reaction notes

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