1-(2-Methoxyphenyl)piperazine → HCID 70619852, compound

HRID 1679555Notes

Reaction equation

HRID 1679555 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]2[CH2:9][CH:8]3[O:15][CH:7]3[CH2:6][C:5]=2[CH:4]=1.[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>[CH3:14][O:13][C:12]1[CH:11]=[C:10]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[CH2:6][C@@H:7]([OH:15])[C@H:8]([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)[CH2:9]2

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 3776IsopropanolHCID 13777158HCID 13777158, compound

Product 1

HCID 70619852HCID 70619852, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 2.94 g of 2,3-dimethoxy-6,7-epoxy-5,6,7,8-tetrahydronaphthalene, 2.9 g of 1-(o-methoxyphenyl)piperazine, and 1 ml of isopropanol in 30 ml of xylene is refluxed for 5 days. The reaction mixture is concentrated in vacuo, the residue taken up in ethyl acetate, and this is thoroughly extracted with dilute hydrochloric acid. The combined acid extracts are made basic with dilute sodium hydroxide solution, and this is thoroughly extracted with ethyl acetate. The combined ethyl acetate extracts are dried and concentrated in vacuo to an oil, which gives 1.3 g of solid on trituration with ethyl acetate. Recrystallization from ethyl acetate gives 600 mg of the title compound, melting point 172°-174° C.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. extractionthis is thoroughly extracted with dilute hydrochloric acid
  3. extractionthis is thoroughly extracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate extracts are dried
  5. concentrationconcentrated in vacuo to an oil, which

Sources & evidence

ORD record
ord-14b6073ffb744db58677cb88246394e4
Source dataset
uspto-grants-1978_03
Patent number
US04081444

Reaction notes

Loading…