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

HRID 2107476Notes

Reaction equation

HRID 2107476 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.[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.[Br-].CO.C(Cl)[Cl:53]>C(OCC)(=O)C.C(#N)C>[ClH:53].[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][N:24]([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)[CH2:23][CH2:22]1

Participants

9

Reactant 6

HCID 259Bromide ionHCID 11430Potassium CarbonateHCID 919652-MeppHCID 1859152-NaphthylalanineHCID 106117723-(4-Bromobutyl)-5,5-dimethyl-4-thiazolidinoneHCID 21226129Dichloromethane methanol

Product 1

HCID 148561473-[4-[1-(2-Methylphenyl)-4-piperazinyl]butyl]5,5-dimethyl-4-thiazolidinone hydrochloride

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3-(4-bromobutyl)-5,5-dimethyl-4-thiazolidinone (4.00 g), 1-(2-methylphenyl)-piperazine (3.87 g), K2CO3 (8.31 g), Nal (290 mg) and acetonitrile (175 ml) was heated at 75° C. (bath temperature) under nitrogen. After 16 hours, TLC analysis (silica gel, 5% MeOH/CH2Cl2) showed absence of the starting bromide and presence of a major product, Rf =0.24. The reaction mixture was cooled to room temperature, ethyl acetate (150 ml) was added, and the mixture filtered. The filtrate was concentrated in vacuo to an oil which was dissolved into ethyl acetate causing a solid to precipitate. The mixture was filtered and the filtrate concentrated in vacuo to 6.35 g of an oil. The oil was chromatographed (5% MeOH/CH2Cl2, one silica gel column) to obtain 4.91 g of a solid. The solid was dissolved in diethylether (550 ml), the solution filtered to remove a trace of insoluble material, and the filtrate acidified to pH=1 with a HCl/diethylether solution. The resulting salt was collected and dried to give 4.83 g of powder. The powder was recrystallized twice from ethanol/ethyl acetate to yield 2.14 g of crystals. m.p. 230°-235° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe mixture filtered
  3. concentrationThe filtrate was concentrated in vacuo to an oil which
  4. dissolutionwas dissolved into ethyl acetate causing a solid
  5. customto precipitate
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate concentrated in vacuo to 6.35 g of an oil
  8. customThe oil was chromatographed (5% MeOH/CH2Cl2, one silica gel column)

Sources & evidence

ORD record
ord-d60986fac2f84ad9be34c131d209dc9d
Source dataset
uspto-grants-1990_06
Patent number
US04933453

Reaction notes

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