Propargyl bromide → 2-Propynylpiperazine

HRID 437824Notes

Reaction equation

HRID 437824 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].COC1C=CC2CC([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)C3C=C(C)C=CC=3OC=2C=1.[CH2:31](Br)[C:32]#[CH:33]>C(O)CCC>[C:31]([CH:21]1[CH2:20][NH:19][CH2:24][CH2:23][NH:22]1)#[C:32][CH3:33]

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 665838092-Propynylpiperazine

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-propynylpiperazine 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-66ef0b4ead964a0f92737c82963b791c
Source dataset
uspto-grants-1977_06
Patent number
US04032525

Reaction notes

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