Propargyl bromide → HCID 22767857, compound

HRID 372437Notes

Reaction equation

HRID 372437 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Cl:7][C:8]1[CH:29]=[CH:28][C:11]2[O:12][C:13]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:14]=3[CH:15]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH2:16][C:10]=2[CH:9]=1.[CH2:30](Br)[C:31]#[CH:32]>C(O)C>[Cl:7][C:8]1[CH:29]=[CH:28][C:11]2[O:12][C:13]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:14]=3[CH:15]([N:17]3[CH2:22][CH2:21][N:20]([CH2:32][C:31]#[CH:30])[CH2:19][CH2:18]3)[CH2:16][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10340Sodium CarbonateHCID 22767945HCID 22767945, compound

Product 1

HCID 22767857HCID 22767857, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2.87 G. of sodium carbonate are added to a solution of 7.6 g. of 1-[2,8-dichloro-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-piperazine in 76 ml. of ethanol. Then, a solution of 1.9 ml. of propargyl bromide in 15 ml. of ethanol is added dropwise with stirring. The mixture is stirred for 20 hours at room temperature and the solvent is then evaporated under reduced pressure. The residue is partitioned between water and chloroform. The phases are separated. The aqueous solution is extracted again with chloroform. The chloroform solutions are washed with water, dried over sodium sulfate and evaporated under reduced pressure. The residue is crystallized using diisopropyl ether, and there is obtained 1-[2,8-dichloro-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-4-(2-propynyl)-piperazine having a melting point of 105°-107° C. The dihydrochloride, prepared in ethanol, melts at 213°-215° C. (with decomposition).

Workup

  1. stirringThe mixture is stirred for 20 hours at room temperature
  2. customthe solvent is then evaporated under reduced pressure
  3. customThe residue is partitioned between water and chloroform
  4. customThe phases are separated
  5. extractionThe aqueous solution is extracted again with chloroform
  6. washThe chloroform solutions are washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue is crystallized

Sources & evidence

ORD record
ord-d3991da7ba5640c7bf136820790a0404
Source dataset
uspto-grants-1978_05
Patent number
US04091023

Reaction notes

Loading…