Hydrochloric Acid → 4-(4-{2-Hydroxy-3-[(naphthalen-1-yl)oxy]propyl}piperazin-1-yl)-3-methoxyphenol

HRID 2247844Notes

Reaction equation

HRID 2247844 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[C:16]1([O:26][CH2:27][CH:28]2[O:30][CH2:29]2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.C(O)(C)C.Cl>CO.C(OCC)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:29][CH:28]([OH:30])[CH2:27][O:26][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 915212-((1-Naphthalenyloxy)methyl)oxiraneHCID 14966308HCID 14966308, compound

Product 1

HCID 1314914-(4-{2-Hydroxy-3-[(naphthalen-1-yl)oxy]propyl}piperazin-1-yl)-3-methoxyphenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.16 g. (0.02 mole) 1-(2-methoxy-4-hydroxyphenyl)-piperazine and 4.2 g. (0.021 mole) 2,3-epoxypropyl naphthyl ether in 50 ml. isopropanol is heated under reflux for 4 hours, while stirring. The solution is evaporated and the tarry residue obtained is dissolved in methanol. It is acidified with isopropanolic hydrochloric acid and diethyl ether carefully added thereto, an oily product precipitating out which is separated by decanting off. The solution is diluted with acetone. After a short time, the compound begins to crystallise out. When crystallisation is complete, the crystals are filtered off with suction and again recrystallised from methanol/diethyl either. Yield 4.8 g. (50% of theory); m.p. 230°-232° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe solution is evaporated
  3. customthe tarry residue obtained
  4. additioncarefully added
  5. customan oily product precipitating out which
  6. customis separated
  7. customby decanting off
  8. additionThe solution is diluted with acetone
  9. customto crystallise out
  10. customWhen crystallisation
  11. filtrationthe crystals are filtered off with suction
  12. customagain recrystallised from methanol/diethyl either

Sources & evidence

ORD record
ord-82f7cfa5078c448494299f8eb40bc5d3
Source dataset
uspto-grants-1991_08
Patent number
US05037828

Reaction notes

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