1-(2-Methoxyphenyl)piperazine → HCID 70619452, compound

HRID 1679550Notes

Reaction equation

HRID 1679550 reaction equation
[O:1]1[CH:11]2[CH:2]1[CH2:3][C:4]1[C:5]([O:14][CH3:15])=[CH:6][CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[CH2:10]2.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(O)(C)C>C1(C)C(C)=CC=CC=1>[CH3:15][O:14][C:5]1[CH:6]=[CH:7][C:8]([O:12][CH3:13])=[C:9]2[C:4]=1[CH2:3][C@@H:2]([N:27]1[CH2:26][CH2:25][N:24]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[O:17][CH3:16])[CH2:29][CH2:28]1)[C@H:11]([OH:1])[CH2:10]2

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 3776IsopropanolHCID 123670031a,2,7,7a-Tetrahydro-3,6-dimethoxynaphth[2,3-b]oxirene

Product 1

HCID 70619452HCID 70619452, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 4.12 g of 6,7-epoxy-5,6,7,8-tetrahydro1,4-dimethoxynaphthalene, 4.81 g of 1-(o-methoxyphenyl)piperazine, and 1.53 ml of isopropyl alcohol in 20 ml of xylene is refluxed under nitrogen for 19 hours. The xylene is removed in vacuo and the residue triturated with ether to give 4.01 g of crude material. Two recrystallizations of this material from ethyl acetate yield 2.5 g of the title compound, melting point 182°-183° C.

Workup

  1. customThe xylene is removed in vacuo
  2. customthe residue triturated with ether

Sources & evidence

ORD record
ord-f038e57e03be4992b52f53d6932ef122
Source dataset
uspto-grants-1978_03
Patent number
US04081444

Reaction notes

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