Methylamine → 2,3,4,9-Tetrahydro-N-methyl-1H-carbazol-3-amine

HRID 427139Notes

Reaction equation

HRID 427139 reaction equation
S(O[CH:12]1[CH2:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]=2[CH2:14][CH2:13]1)(C1C=CC(C)=CC=1)(=O)=O.[CH3:25][NH2:26].C(OCCO)C.C(=O)(O)[O-].[Na+]>>[CH3:25][NH:26][CH:12]1[CH2:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]=2[CH2:14][CH2:13]1

Participants

5

Reactant 4

HCID 6329MethylamineHCID 8076Glycol monoethyl etherHCID 516892Sodium BicarbonateHCID 123617693-Tosyloxy-1,2,3,4-tetrahydrocarbazole

Product 1

HCID 1524452,3,4,9-Tetrahydro-N-methyl-1H-carbazol-3-amine

Procedure

A mixture of 17 g. of 3-tosyloxy-1,2,3,4-tetrahydrocarbazole and 25 g. of 40% methylamine in 200 ml. of 2-ethoxyethanol containing 5 g. of sodium bicarbonate was heated on a steam bath for one hour then left standing overnight at room temperature. The solvent was removed by distillation and the residue taken up in ether and the mixture filtered. Evaporation of the filtrate gave a residue which crystallized upon trituration with ether. The 3-(methylamino)-1,2,3,4-tetrahydrocarbazole thus obtained melted at 134°-136° C. (corr.).

Workup

  1. additionA mixture of 17 g
  2. waitthen left
  3. customThe solvent was removed by distillation
  4. filtrationthe mixture filtered
  5. customEvaporation of the filtrate
  6. customgave a residue which
  7. customcrystallized upon trituration with ether

Sources & evidence

ORD record
ord-635bbb00d8e24cf6aa0904f92da84897
Source dataset
uspto-grants-1979_10
Patent number
US04172834

Reaction notes

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