1-(2-Methoxyphenyl)piperazine → HCID 70619596, compound

HRID 328701Notes

Reaction equation

HRID 328701 reaction equation
[O:1]1[CH:11]2[CH:2]1[CH2:3][C:4]1[C:5]([O:16]C(=O)C)=[CH:6][CH:7]=[C:8]([O:12]C(=O)C)[C:9]=1[CH2:10]2.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C1(C)C(C)=CC=CC=1>[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][N:31]([C@@H:2]2[CH2:3][C:4]3[C:5]([OH:16])=[CH:6][CH:7]=[C:8]([OH:12])[C:9]=3[CH2:10][C@H:11]2[OH:1])[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 331538(3-acetyloxy-1a,2,7,7a-tetrahydronaphtho[6,7-b]oxiren-6-yl) acetate

Product 1

HCID 70619596HCID 70619596, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 13.1 g of 6,7-epoxy-5,6,7,8-tetrahydro-1,4-diacetoxynaphthalene and 29.8 g of 1-(o-methoxyphenyl)piperazine in 200 ml of xylene is refluxed under nitrogen for 48 hours. The reaction mixture is then cooled, the crystalline precipitate filtered, washed with ether, and dried in vacuo to afford 10.55 g of crude crystalline product. Recrystallization of 7.50 g of this material from ethyl acetate/ethanol gives 4.0 g of the title compound, melting point 222°-224° C.

Workup

  1. temperatureThe reaction mixture is then cooled
  2. filtrationthe crystalline precipitate filtered
  3. washwashed with ether
  4. customdried in vacuo
  5. customto afford 10.55 g of crude crystalline product
  6. customRecrystallization of 7.50 g of this material from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-12c430fa591e438cbbb52f8e6b48dbd1
Source dataset
uspto-grants-1977_04
Patent number
US04018773

Reaction notes

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