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

HRID 461544Notes

Reaction equation

HRID 461544 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 1 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-804a90c840084bf6a17ddaa095871f96
Source dataset
uspto-grants-1977_12
Patent number
US04062864

Reaction notes

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