Benzene, (chloromethyl)phenoxy- → (E)-1-[[(2-phenoxyphenyl)methoxy]ethyl]-4-(3-phenyl-2-propenyl)piperazine dihydrochloride

HRID 728798Notes

Reaction equation

HRID 728798 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10][Cl:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1(/[CH:22]=[CH:23]/[CH2:24][N:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][OH:33])[CH2:27][CH2:26]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(OC(C)(C)C)(C)(C)C.[K]>C(COC)OC>[ClH:11].[ClH:11].[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10][O:33][CH2:32][CH2:31][N:28]1[CH2:29][CH2:30][N:25]([CH2:24]/[CH:23]=[CH:22]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:26][CH2:27]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 169302Benzene, (chloromethyl)phenoxy-HCID 782659(E)-4-(3-phenyl-2-propenyl)-1-piperazineethanolHCID 86607002Potassium tert-butyloxide

Product 1

HCID 67898433(E)-1-[[(2-phenoxyphenyl)methoxy]ethyl]-4-(3-phenyl-2-propenyl)piperazine dihydrochloride

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

7.82 g (3.58 mmol) of o-phenoxybenzyl chloride dissolved in 8 ml of dimethoxyethane were added dropwise at room temperature to a solution of 8.82 g (35.8 mmol) of (E)-4-(3-phenyl-2-propenyl)-1-piperazineethanol and 4.42 g (39.4 mmol) of potassium tert-butyloxide and 4 g of 3A molecular sieve in 125 ml of dry dimethoxyethane. After stirring for 3 days at 40° C., the mixture was cooled to room temperature. The salts in the solution were filtered off and the solution was evaporated. The residue obtained was purified by means of column chromatography over silica (eluent toluene:ethanol=9:1). The collected fractions were dissolved in ethanol and 5 ml of 4.9 N HCl in ethanol was added. The clearsolution was evaporated. Yield 2.4 g (13%), m.p. 221° C.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationThe salts in the solution were filtered off
  3. customthe solution was evaporated
  4. customThe residue obtained
  5. customwas purified by means of column chromatography over silica (eluent toluene:ethanol=9:1)
  6. dissolutionThe collected fractions were dissolved in ethanol
  7. addition5 ml of 4.9 N HCl in ethanol was added
  8. customThe clearsolution was evaporated

Sources & evidence

ORD record
ord-861e18a1faba469dbd6884b7c8c75614
Source dataset
uspto-grants-1991_09
Patent number
US05051424

Reaction notes

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