2-((1-Naphthalenyloxy)methyl)oxirane → HCID 11596312, compound

HRID 1973551Notes

Reaction equation

HRID 1973551 reaction equation
[O:1]1[CH2:15][CH:2]1[CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1>C(O)C>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH2:15][CH:2]([OH:1])[CH2:3][O:4][C:5]3[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH:8]=[CH:7][CH:6]=3)[CH2:26][CH2:25]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 915212-((1-Naphthalenyloxy)methyl)oxiraneHCID 2697221-(4-Methoxyphenyl)piperazine

Product 1

HCID 11596312HCID 11596312, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20.0 g. (0.1 mol) 2,3-epoxy-1-(1-naphthyloxy)-propane were mixed with 30 ml. ethanol and 19.2 g. (0.1 mol) 1-(4-methoxyphenyl)-piperazine, whereafter the reaction mixture was heated to 60° C. and maintained at this temperature for 6 hours. The reaction mixture was then left to stand overnight and the ethanol subsequently evaporated off. The oily residue was dissolved in chloroform, hydrogen chloride was passed through the chloroform solution and then ether was added, the dihydrochloride thereby precipitating out. This was filtered off with suction and recrystallized from methanol/ethanol (1:3). There was obtained 1-(4-methoxy-phenyl)-4-[3-(naphth-1-yloxy)-2-hydroxypropyl]-piperazine in a yield of 76% of theory. The product had a melting point of 237° - 238° C.

Workup

  1. temperaturemaintained at this temperature for 6 hours
  2. waitThe reaction mixture was then left
  3. customthe ethanol subsequently evaporated off
  4. dissolutionThe oily residue was dissolved in chloroform
  5. additionether was added
  6. customthe dihydrochloride thereby precipitating out
  7. filtrationThis was filtered off with suction
  8. customrecrystallized from methanol/ethanol (1:3)

Sources & evidence

ORD record
ord-b3ca571efe2647fbb000104fe8b64fe9
Source dataset
uspto-grants-1976_12
Patent number
US03997666

Reaction notes

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