Diazomethane → HCID 70619348, compound

HRID 1679553Notes

Reaction equation

HRID 1679553 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([C@@H:15]2[CH2:24][C:23]3[C:22]([OH:25])=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:17][C@H:16]2[OH:26])[CH2:11][CH2:10]1.[N+](=[CH2:29])=[N-]>CO>[CH3:29][O:25][C:22]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:23]=1[CH2:24][C@@H:15]([N:12]1[CH2:11][CH2:10][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:14][CH2:13]1)[C@H:16]([OH:26])[CH2:17]2

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 70619651HCID 70619651, compound

Product 1

HCID 70619348HCID 70619348, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.0 g of trans-5,6,7,8-tetrahydro-7-[4-(2-methoxyphenyl)-1-piperazinyl]-1,6-naphthalenediol in methanol is treated with about 2 equivalents of freshly prepared diazomethane. The solution is stored at 0° C for 48 hours. The solvent is removed in vacuo, the residue is dissolved in ethyl acetate and washed with dilute sodium hydroxide solution. After drying and removal of solvent in vacuo, an oil remains which crystallizes on trituration with a very small amount of ether. The crystalline material is washed with a small amount of isopropyl ether and recrystallized from etherisopropyl ether to give 1.13 g of the title compound, melting point 138°-141° C.

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with dilute sodium hydroxide solution
  4. customAfter drying
  5. customremoval of solvent in vacuo
  6. customcrystallizes on trituration with a very small amount of ether
  7. washThe crystalline material is washed with a small amount of isopropyl ether
  8. customrecrystallized from etherisopropyl ether

Sources & evidence

ORD record
ord-549ee8da2e884e47a459de0612d81775
Source dataset
uspto-grants-1978_03
Patent number
US04081444

Reaction notes

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