Propargyl bromide → 1-[10,11-Dihydro-3-methoxy-8-methyl-dibenz[b,f]oxepin-10-yl]-4-(2-propynyl)piperazine

HRID 866615Notes

Reaction equation

HRID 866615 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:18][CH:17]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:16]3[CH:25]=[C:26]([CH3:29])[CH:27]=[CH:28][C:15]=3[O:14][C:13]=2[CH:30]=1.[CH2:31](Br)[C:32]#[CH:33]>C(O)CCC>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:18][CH:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:33][C:32]#[CH:31])[CH2:21][CH2:20]3)[C:16]3[CH:25]=[C:26]([CH3:29])[CH:27]=[CH:28][C:15]=3[O:14][C:13]=2[CH:30]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10340Sodium CarbonateHCID 227679281-[10,11-Dihydro-3-methoxy-8-methyl-dibenz[b,f]oxepin-10-yl]-piperazine

Product 1

HCID 227678361-[10,11-Dihydro-3-methoxy-8-methyl-dibenz[b,f]oxepin-10-yl]-4-(2-propynyl)piperazine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

3.8 G. of sodium carbonate are added to a solution of 10 g. of 1-[10,11-dihydro-3-methoxy-8-methyl-dibenz[b,f]oxepin-10-yl]-piperazine in 55 ml. of butanol and then a solution of 2.5 ml. of propargyl bromide in 20 ml. of butanol is added dropwise. Then, the mixture is stirred for 20 hours at room temperature and the solvent is removed by distillation under reduced pressure. After working-up in an analogous manner to that described in Example 13, there is isolated crude 1-[10,11-dihydro-3-methoxy-8-methyl-dibenz[b,f]oxepin-10-yl]-4-(2-propynyl)piperazine in the form of an oil. The dihydrochloride, prepared in ethanol and recrystallized from methanol/ether, melts at 210°-212° C. (with decomposition).

Workup

  1. customthe solvent is removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-b40ac20b22c0459898991ba7a4e26491
Source dataset
uspto-grants-1978_07
Patent number
US04100173

Reaction notes

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