1-(2-Methoxyphenyl)piperazine → HCID 14856167, compound

HRID 1491906Notes

Reaction equation

HRID 1491906 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[CH2:9][S:8](=[O:12])[CH2:7]1.[CH3:13][O: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+].CC#N>[Na+].[I-].CO.C(Cl)Cl>[CH3:13][O: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])[CH2:9][S:8](=[O:12])[CH2:7]2)[CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 21706595HCID 21706595, compound

Product 1

HCID 14856167HCID 14856167, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 3-(4-bromobutyl)-1,4-dioxothiazolidine (3.37 g), 1-(2-methoxyphenyl)piperazine (2.80 g), K2CO3 (4.60 g), NaI (190 mg) and CH3CN (150 ml) was heated at reflux (bath temperature 95° C.) for 24 h. TLC analysis (silica gel, 20% MeOH/CH2Cl2) showed the consumption of the starting sulfoxide and the presence of one major product with Rf =0.43. The mixture was cooled to room temperature, EtOAc (100 m) was added and the mixture was filtered. The filtrate was concentrated in vacuo to an oil which was filtered through silica gel using 20% MeOH/CH2Cl2 as the eluent. The fractions containing the material with Rf =0.43 were concentrated in vacuo to yield 4.83 g of a foam, which was dissolved in MeOH/CH2Cl2 and flash chromatographed (silica gel) to yield 3.28 g of a crude product. Rechromatography over silica gel using 50% MeOH/toluene as eluent yielded 2.98 g of an oil which solidified on standing. The solid was dissolved in 50% MeOH/EtOAc and filtered through silica gel. The filtrate containing the product was concentrated to approximately 5 ml and the oily liquid was seeded and left standing, yielding 0.91 g of a white solid, mp, 111°-113° C. The mother liquor was concentrated in vacuo to a solid which was recrystallized from CH2Cl2 /Et2O yielding an additional 0.79 g of fine needles, mp, 111°-113° C.

Workup

  1. temperaturewas heated
  2. customthe consumption of the starting sulfoxide
  3. temperatureThe mixture was cooled to room temperature
  4. additionEtOAc (100 m) was added
  5. filtrationthe mixture was filtered
  6. concentrationThe filtrate was concentrated in vacuo to an oil which
  7. filtrationwas filtered through silica gel using 20% MeOH/CH2Cl2 as the eluent
  8. additionThe fractions containing the material with Rf =0.43
  9. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-b2bed5281c22426eab680a229e2fca21
Source dataset
uspto-grants-1994_12
Patent number
US05371087

Reaction notes

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