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

HRID 2247843Notes

Reaction equation

HRID 2247843 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[C:14]1([O:24][CH2:25][CH:26]2[O:28][CH2:27]2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.Cl>C(O)(C)C>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:27][CH:26]([OH:28])[CH2:25][O:24][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 70530o-(1-Piperazinyl)phenolHCID 915212-((1-Naphthalenyloxy)methyl)oxirane

Product 1

HCID 1314902-(4-{2-Hydroxy-3-[(naphthalen-1-yl)oxy]propyl}piperazin-1-yl)phenol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

4.56 g. (0.025 mole) 1-(2-hydroxyphenyl)-piperazine and 5.6 g. (0.028 mole) 2,3-epoxypropyl naphthyl ether are dissolved in 50 ml. isopropanol and the solution obtained is heated under reflux for 5 hours, while stirring. Thereafter, the reaction mixture is diluted with a further 50 ml. isopropanol and acidified isopropanolic hydrochloric acid. A voluminous product precipitates out which is filtered off with suction, washed several times with isopropanol and recrystallised from methanol. Yield 8.8 g. (77% of theory); m.p. 249°-250° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 5 hours
  3. additionThereafter, the reaction mixture is diluted with a further 50 ml
  4. customA voluminous product precipitates out which
  5. filtrationis filtered off with suction
  6. washwashed several times with isopropanol
  7. customrecrystallised from methanol

Sources & evidence

ORD record
ord-9bff4c8e78374c90bbd23174a122af5c
Source dataset
uspto-grants-1991_08
Patent number
US05037828

Reaction notes

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