Acetone → HCID 68420671, compound

HRID 1710474Notes

Reaction equation

HRID 1710474 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[S:27])=[CH:21][CH:20]=1.[CH3:28]C(C)=O>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:26]([S:27][CH3:28])=[N:25][C:22]2[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 752934-Methoxyphenyl isothiocyanateHCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 68420671HCID 68420671, compound

Procedure

1-Benzyloxycarbonylpiperazine (6.35 g) was dissolved in acetone (40 mL) and 4-methoxyphenyl isothiocyanate (5.19 g) were added under ice-cooling. The mixture was stirred at room temperature for 2 days. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in dichloromethane (80 mL). Methyl iodide (2.7 mL) was added under ice-cooling, and the mixture was stirred at room temperature for 17 hr. The reaction solution was added to a saturated a aqueous sodium hydrogen carbonate solution, and the mixture was extracted with dichloromethane. The extract solution washed with saturated brine, dried and concentrated under reduced pressure to give 1-benzyloxycarbonyl-4-[(methylthio)(4-methoxyphenyl)iminomethyl]piperazine (12.8 g) as a brown oil.

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane (80 mL)
  4. additionMethyl iodide (2.7 mL) was added under ice-
  5. temperaturecooling
  6. stirringthe mixture was stirred at room temperature for 17 hr
  7. additionThe reaction solution was added to a saturated a aqueous sodium hydrogen carbonate solution
  8. extractionthe mixture was extracted with dichloromethane
  9. washThe extract solution washed with saturated brine
  10. customdried
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e5e46b94e2c048e19ea16de161104af1
Source dataset
uspto-grants-2010_09
Patent number
US07790725B2

Reaction notes

Loading…