N-[2-(9-ethyl-1,2,3,4-tetrahydro-1-methylcarbazol-1-yl)ethyl]-N-methylformamide → 9-Ethyl-1,2,3,4-tetrahydro-N,1-dimethylcarbazole-1-ethanamine

HRID 65629Notes

Reaction equation

HRID 65629 reaction equation
[CH2:1]([N:3]1[C:15]2[C:14]([CH2:17][CH2:18][N:19](C)[CH:20]=O)([CH3:16])[CH2:13][CH2:12][CH2:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]>[OH-].[K+]>[CH2:1]([N:3]1[C:15]2[C:14]([CH3:16])([CH2:17][CH2:18][NH:19][CH3:20])[CH2:13][CH2:12][CH2:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

3

Reactant 1

HCID 12291913N-[2-(9-ethyl-1,2,3,4-tetrahydro-1-methylcarbazol-1-yl)ethyl]-N-methylformamide

Product 1

HCID 429029-Ethyl-1,2,3,4-tetrahydro-N,1-dimethylcarbazole-1-ethanamine

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

N-[2-(9-ethyl-1,2,3,4-tetrahydro-1-methylcarbazol-1-yl)ethyl]-N-methylformamide (2.1 g), described in Example 225, is heated at reflux in a solution of 10% KOH (50 ml) for 48 hr. After cooling the solution is rendered acidic and extracted with ether. The aqueous phase is then rendered alkaline and extracted with ether. The latter extract is dried (MgSO4) and conc. to yield the title compound, nmr (CDCl3) δ 1.4 (m, 6H), 2.37 (s, 3H), 4.3 (q, J = 7, 2H), 7.25 (m, 4H); the corresponding hydrochloric acid addition salt has mp 213°-216° C.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling the solution
  3. extractionextracted with ether
  4. extractionextracted with ether
  5. extractionThe latter extract
  6. dry with materialis dried (MgSO4)

Sources & evidence

ORD record
ord-17a44a83b2f5411c9dc9612e31dd19eb
Source dataset
uspto-grants-1978_12
Patent number
US04128560

Reaction notes

Loading…