Potassium Permanganate → Mazindol

HRID 1580989Notes

Reaction equation

HRID 1580989 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][NH:14][CH2:13][CH2:12][NH:11]2)=[CH:6][CH:5]=1.[Mn]([O-])(=O)(=O)=[O:23].[K+]>O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([OH:23])[C:17]3[C:16](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15]3=[N:14][CH2:13][CH2:12][N:11]23)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 681340411-(4-Chlorophenyl)-1,2,3,4,5,6-hexahydro-2,5-benzodiazocine--hydrogen chloride (1/2)

Product 1

HCID 4020Mazindol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Two grams of 1-(p-chlorophenyl)-1,2,3,4,5,6-hexahydro-2,5-benzodiazocine dihydrochloride are dissolved in 50 ml. of water. A solution of 1 g. of potassium permanganate in 50 ml. of water is added dropwise over a period of one-half hour. The mixture is filtered to remove inorganic salts and the filtrate is made basic with sodium carbonate solution. The precipitated solid is separated and washed with water. On recrystallization from ethanol there is obtained 5-(4-chlorophenyl)-2,3-dihydro-5H-imidazo [2,1-a]isoindol-5-ol which has the same physical characteristics as the identical compound of Example X.

Workup

  1. filtrationThe mixture is filtered
  2. customto remove inorganic salts
  3. customThe precipitated solid is separated
  4. washwashed with water
  5. customOn recrystallization from ethanol

Sources & evidence

ORD record
ord-432bfa76e7be42b7ae6706f73d8af0c7
Source dataset
uspto-grants-1976_01
Patent number
US03935218

Reaction notes

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