Bromide ion → 3-[4-[1-(2-Benzothiazolyl)-4-piperazinyl]butyl]-5,5-dimethyl-4-thiazolidinone

HRID 484138Notes

Reaction equation

HRID 484138 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[S:8][CH2:7]1.[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[Br-]>C(OCC)(=O)C.CO.C(Cl)Cl.C(#N)C>[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[N:23]1[CH2:24][CH2:25][N:26]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[S:8][CH2:7]2)[CH2:27][CH2:28]1

Participants

9

Reactant 5

HCID 259Bromide ionHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 5921222-Piperazin-1-yl-1,3-benzothiazoleHCID 106117723-(4-Bromobutyl)-5,5-dimethyl-4-thiazolidinone

Product 1

HCID 105733073-[4-[1-(2-Benzothiazolyl)-4-piperazinyl]butyl]-5,5-dimethyl-4-thiazolidinoneYield 77.9%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-(4-bromobutyl)-5,5-dimethyl-4-thiazolidinone (3.42 g), 1-(2-benzothiazolyl)piperazine (3.10 g), K2CO3 (6.19 g), NaI (250 mg) and acetonitrile was heated at 65° C. (bath temperature) under nitrogen. After 19 hours, TLC analysis (5% methanol/methylene chloride) showed the absence of starting bromide and the presence of a major product, Rf =0.29. The reaction mixture was cooled to room temperature, ethyl acetate (100 ml) was added and the mixture filtered. The filtrate was concentrated in vacuo to a solid which was redissolved in hot ethyl acetate causing a solid to precipitate. The mixture was filtered and the filtrate concentrated in vacuo to an off-white solid. Chromatography of the crude product by HPLC (Waters Prep 500, one silica gel column, 5% methanol/methylene chloride) yielded 4.05 g of a solid, mp 99.5°-100.5° C. It was recrystallized from methylene chloride/hexane to give 2.83 g of fine needles, mp 101°-102° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe mixture filtered
  3. concentrationThe filtrate was concentrated in vacuo to a solid which
  4. dissolutionwas redissolved in hot ethyl acetate causing a solid
  5. customto precipitate
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate concentrated in vacuo to an off-white solid

Sources & evidence

ORD record
ord-744eb17cacb540229a64060f62c9185a
Source dataset
uspto-grants-1993_07
Patent number
US05229388

Reaction notes

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