Bromide ion → HCID 14856155, compound

HRID 2392785Notes

Reaction equation

HRID 2392785 reaction equation
[CH3:1][C:2]1([CH3:13])[N:6]([CH2:7][CH2:8][CH2:9][CH2:10]Br)[C:5](=[O:12])[CH2:4][S:3]1.[CH3:14][C:15]1[CH:16]=[C:17]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[Cl:35]Cl.[Br-]>CCOC(C)=O.CCO.CC#N>[ClH:35].[ClH:35].[CH3:1][C:2]1([CH3:13])[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][N:24]2[CH2:25][CH2:26][N:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([CH3:14])[CH:16]=3)[CH2:22][CH2:23]2)[C:5](=[O:12])[CH2:4][S:3]1

Participants

10

Reactant 6

HCID 259Bromide ionHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 24526ChlorineHCID 831111-(m-Tolyl)piperazineHCID 10754200HCID 10754200, compound

Product 1

HCID 14856155HCID 14856155, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,2-dimethyl-3-(4-bromobutyl)-4-thiazolidinone (4.01 g), 1-(3-methylphenyl)piperazine (3.17 g), K2CO3 (5.30 g), NaI (230 mg) and CH3CN (180 mL) was heated at reflux (oil bath temperature; 100° C.) for 20 h. TLC analysis (silica gel, 7.5% EtOH/CH2 Cl2 showed one major product, Rf =0.53, and a trace of starting bromide, Rf =0.70. The reaction mixture was cooled to room temperature, EtOAc (100 mL) was added and the mixture filtered. The filtrate was concentrated in vacuo to an oil which was triturated with EtOAc (150 mL). The mixture was filtered and the filtrate concentrated in vacuo to an oil. HPLC of the crude oil (Waters Prep 500 silica gel, 8% MeOH/EtOAc) yielded 5.42 g of an oil, Rf =0.53. The hydrochloride salt of this amine was precipitated by the addition of HCl/Et2O to a solution of the base in 600 ml of ether until pH=2 to give 5.30 g of a white powder. Recrystallization from EtOH yielded 2.91 g of white crystals, mp 204° C. (dec).

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe mixture filtered
  4. concentrationThe filtrate was concentrated in vacuo to an oil which
  5. customwas triturated with EtOAc (150 mL)
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate concentrated in vacuo to an oil

Sources & evidence

ORD record
ord-a449c3bc84f841499e0321002c251901
Source dataset
uspto-grants-1998_09
Patent number
US05801186

Reaction notes

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