Ethanol → HCID 70619885, compound

HRID 1679556Notes

Reaction equation

HRID 1679556 reaction equation
[O:1]1[CH:11]2[CH:2]1[CH2:3][C:4]1[C:9]([CH2:10]2)=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:5]=1[O:14][CH3:15].C1(C)C=CC=CC=1[CH:22]1[CH2:27][NH:26][CH2:25][CH2:24][NH:23]1.C(O)C.[C:32]1(C)[C:33]([CH3:38])=[CH:34][CH:35]=[CH:36][CH:37]=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:23]1[CH2:24][CH2:25][N:26]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])[CH2:27][CH2:22]1)[C@H:11]([OH:1])[CH2:10]2

Participants

5

Reactant 4

HCID 702EthanolHCID 7237O-XyleneHCID 123670031a,2,7,7a-Tetrahydro-3,6-dimethoxynaphth[2,3-b]oxireneHCID 55253315HCID 55253315, compound

Product 1

HCID 70619885HCID 70619885, compound

Procedure

A solution of 10.3 g of 2,3-epoxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene, 8.8 g of o-tolylpiperazine, and 2 ml of absolute ethanol in 100 ml of xylene is refluxed for 4 days. The reaction mixture is cooled to room temperature, and the resulting crystalline solid is filtered off and washed with ether to give 15.2 g of crude product. Recrystallization from ethanol/methanol gives 4 g of the title compound, melting point 271°-219° C.

Workup

  1. filtrationthe resulting crystalline solid is filtered off
  2. washwashed with ether
  3. customto give 15.2 g of crude product
  4. customRecrystallization from ethanol/methanol

Sources & evidence

ORD record
ord-c47d8c0e41414af9a06b455a2c5f89ff
Source dataset
uspto-grants-1978_03
Patent number
US04081444

Reaction notes

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