Hydrogen Bromide → HCID 14097029, compound

HRID 4319Notes

Reaction equation

HRID 4319 reaction equation
C[O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][N:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([O:30]C)=[CH:26][CH:25]=4)[CH2:19][CH2:18]3)[CH2:10][CH2:9]2)=[CH:5][CH:4]=1.Br>O>[OH:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:20]2[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][CH2:14][N:11]3[CH2:10][CH2:9][N:8]([CH2:7][C:6]4[CH:5]=[CH:4][C:3]([OH:2])=[CH:33][CH:32]=4)[CH2:13][CH2:12]3)[CH2:18][CH2:19]2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 140970281,3-Bis[4-(4-methoxybenzyl)-1-piperazinyl]propane

Product 1

HCID 14097029HCID 14097029, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.5 g of 1,3-bis[4-(4-methoxybenzyl)-1-piperazinyl]propane from Example 19 and 125 ml of 49% hydrobromic acid was refluxed for 2 hours and was then cooled and diluted with 125 ml of water. After filtration the aqueous solution was neutralized with 2N sodium hydroxide to adjust the pH to 8. The resulting mixture was extracted three times each with 150 ml of ethanol. The alcohol was then removed by rotary evaporation and the residue was chromatographed on silica with the eluant being methylene chloride containing 1% ammonium hydroxide and 10% methanol to obtain 1.3 g (31% of theory) of 1,3-bis[4-(4-hydroxybenzyl)-1-piperazinyl]propane as a white crystalline product, melting at 197°-201° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperaturewas then cooled
  3. filtrationAfter filtration the aqueous solution
  4. extractionThe resulting mixture was extracted three times each with 150 ml of ethanol
  5. customThe alcohol was then removed by rotary evaporation
  6. customthe residue was chromatographed on silica with the eluant

Sources & evidence

ORD record
ord-35f81a39a06a45d1ab9c40a8e88e5022
Source dataset
uspto-grants-1988_02
Patent number
US04725597

Reaction notes

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