Bromide ion → HCID 14856155, compound

HRID 846422Notes

Reaction equation

HRID 846422 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-].[Br-].CCO.C(Cl)[Cl:40]>CCOC(C)=O.CC#N>[ClH:40].[ClH:40].[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

9

Reactant 6

HCID 259Bromide ionHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 831111-(m-Tolyl)piperazineHCID 10754200HCID 10754200, compoundHCID 21584144Dichloromethane ethanol

Product 1

HCID 14856155HCID 14856155, compound

Reagents, catalysts & solvents 2

HCID 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/CH2Cl2 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-ec014a9d9f0547ddb6dff2618640c78f
Source dataset
uspto-grants-1992_08
Patent number
US05136037

Reaction notes

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