1-(2-Methoxyphenyl)piperazine → HCID 10249134, compound

HRID 1381106Notes

Reaction equation

HRID 1381106 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.Br[CH2:16][CH2:17][CH2:18][N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH2:18][N:19]2[C:23](=[O:24])[C:22]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]3[C:20]2=[O:29])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 11430Potassium CarbonateHCID 21611N-3-Bromopropylphthalimide

Product 1

HCID 10249134HCID 10249134, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(o-methoxyphenyl)piperazine (0.19 mol), N-(3-bromopropyl)phthalimide (0.186 mol) and micropulverized potassium carbonate (0.465 mol) in acetonitrile (375 ml) was heated at reflux for 16 hours. The cooled mixture was evaporated in vacuo and the residue diluted with water (800 ml) and extracted with chloroform (4×350 ml). After drying (MgSO4), the combined extracts were evaporated in vacuo. The residue was dried under high vacuum (<0.05 mm of Hg) at room temperature for 16 hours resulting in 72.0 g of a yellow solid ~100% yield); mp 85°-93° C. Spectral data were consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customThe cooled mixture was evaporated in vacuo
  4. additionthe residue diluted with water (800 ml)
  5. extractionextracted with chloroform (4×350 ml)
  6. dry with materialAfter drying (MgSO4)
  7. customthe combined extracts were evaporated in vacuo
  8. customThe residue was dried under high vacuum (<0.05 mm of Hg) at room temperature for 16 hours

Sources & evidence

ORD record
ord-447b97f34d084141b500679ef70dec94
Source dataset
uspto-grants-1986_04
Patent number
US04585773

Reaction notes

Loading…