Dimethylformamide → HCID 13688008, compound

HRID 2290284Notes

Reaction equation

HRID 2290284 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7](Cl)[C:6]=2[CH:17]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([N:22]3[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]3)[C:6]=2[CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 531671-MethylpiperazineHCID 13753408HCID 13753408, compound

Product 1

HCID 13688008HCID 13688008, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.00 gram (3.27 millimoles) of 3-bromo-5-chloro-5H-dibenzo[a,d]cycloheptene, 0.7 gram (about 7 millimoles) of N-methylpiperazine and 3 milliliters of dimethylformamide were stirred together at room temperature under an atmosphere of nitrogen for 60 hours. At the end of this period, water and aqueous sodium carbonate solution was added, and the resulting aqueous solution extracted with ether. The ether solution was washed five times with water, then with saturated sodium chloride solution and dried over magnesium sulfate. The solvent was removed from the dried solution in vacuo to obtain a residue. The residue was triturated with acetonitrile and crystallized from acetonitrile. It was then purified by passing through a Still column using 3 percent methanol in chloroform as eluant, crystallized from acetonitrile, and the crystals dried over phosphorus pentoxide at 78° C./0.2 mm Hg for 17 hours to obtain 0.57 gram of 1-(3-bromo-5H-dibenzo[a,d]cyclohepten-5-yl)-4-methylpiperazine product, m.p. 128°-130° C. Elemental analyses were as follows:

Workup

  1. extractionthe resulting aqueous solution extracted with ether
  2. washThe ether solution was washed five times with water
  3. dry with materialwith saturated sodium chloride solution and dried over magnesium sulfate
  4. customThe solvent was removed from the dried solution in vacuo
  5. customto obtain a residue
  6. customThe residue was triturated with acetonitrile
  7. customcrystallized from acetonitrile
  8. customIt was then purified
  9. customcrystallized from acetonitrile
  10. dry with materialthe crystals dried over phosphorus pentoxide at 78° C./0.2 mm Hg for 17 hours

Sources & evidence

ORD record
ord-78bc31b386c546a8a2e4ddbeb6b3e9a4
Source dataset
uspto-grants-1986_10
Patent number
US04616023

Reaction notes

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