Potassium Carbonate → 1-(5,6-Dimethoxy-2-methylindol-3-ylglyoxyloyl)-4-nitrosopiperazine

HRID 1973406Notes

Reaction equation

HRID 1973406 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7]([CH3:14])=[CH:6]2.C(=O)([O-])[O-].[K+].[K+].[C:21](Cl)(=[O:25])[C:22](Cl)=[O:23].[N:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28]>C(OCC)C.O.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7]([CH3:14])=[C:6]2[C:21](=[O:25])[C:22]([N:32]1[CH2:33][CH2:34][N:29]([N:27]=[O:28])[CH2:30][CH2:31]1)=[O:23]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 21845N-NitrosopiperazineHCID 65578Oxalyl chlorideHCID 2665965,6-dimethoxy-2-methyl-1H-indole

Product 1

HCID 123921981-(5,6-Dimethoxy-2-methylindol-3-ylglyoxyloyl)-4-nitrosopiperazine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A stirred mixture of 3.82 g (0.02 mol) of 5,6-dimethoxy-2-methylindole and 5,80 g (0.044 mol) of potassium carbonate in 50 ml. of chloroform and 15 ml. of water is cooled to -5° C. Then 3.2 g (0.024 mol) of oxalyl chloride is added slowly, maintaining the reaction temperature at 0° C. The resulting mixture is stirred at room temperature for 10 minutes. Then 3.5 g (0.03 mol) of nitrosopiperazine is added over a 5 minute span. The reaction mixture turns red-purple and is stirred for an additional hour. To the solution is slowly added in portions 250 ml. of ethyl ether; the solution appears lighter and a tan precipitate forms. After stirring for one hour, the product is filtered, washed well with water and dried. This product is recrystallized from a DMF and water mixture to give flakes of 1-(5,6-dimethoxy-2-methylindol-3-ylglyoxyloyl)-4-nitrosopiperazine, m.p. 233°-225° C. Analysis: Calculated for C17H20N4O5 : 56.66% C; 5.59% H; 15.55% N Found: 56.65% C; 5.61% H; 15.68% N.

Workup

  1. stirringis stirred for an additional hour
  2. additionTo the solution is slowly added in portions 250 ml
  3. stirringAfter stirring for one hour
  4. filtrationthe product is filtered
  5. washwashed well with water
  6. customdried
  7. customThis product is recrystallized from a DMF and water mixture

Sources & evidence

ORD record
ord-2a319a48969445e8a6e05ec5e852eef7
Source dataset
uspto-grants-1976_12
Patent number
US03997539

Reaction notes

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