N-[2-(1,2,3,4-tetrahydro-1,9-dimethylcarbazol-1-yl)ethyl]-N-methylformamide → N,N,1,9-Tetramethyl-1,2,3,4-tetrahydrocarbazole-1-ethanamine

HRID 65627Notes

Reaction equation

HRID 65627 reaction equation
[CH3:1][C:2]1([CH2:16][CH2:17][N:18]([CH3:21])[CH:19]=O)[C:14]2[N:13]([CH3:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:21][N:18]([CH3:19])[CH2:17][CH2:16][C:2]1([CH3:1])[C:14]2[N:13]([CH3:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 12291917N-[2-(1,2,3,4-tetrahydro-1,9-dimethylcarbazol-1-yl)ethyl]-N-methylformamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 42898N,N,1,9-Tetramethyl-1,2,3,4-tetrahydrocarbazole-1-ethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-[2-(1,2,3,4-tetrahydro-1,9-dimethylcarbazol-1-yl)ethyl]-N-methylformamide (5.0 g, 0.017 mole), described in Example 225, in anhydrous THF (100 ml) is added dropwise to a stirred suspension of lithium aluminium hydride (0.50 g, 0.015 mole) in anhydrous THF (50 ml) under nitrogen. Stirring is continued for 2 hr at 25° C. The excess hydride is destroyed by dropwise addition of water to the cooled mixture. Saturated sodium chloride solution is added and the compound is extracted with ether. The ether solution is dried (MgSO4) and concentraed to yield the title compound, nmr (CDCl3) δ 1.4 (s, 3H), 2.19 (s, 6H), 3.8 (s, 3H), 7.0-7.6 (m, 4H).

Workup

  1. customThe excess hydride is destroyed by dropwise addition of water to the cooled mixture
  2. additionSaturated sodium chloride solution is added
  3. extractionthe compound is extracted with ether
  4. dry with materialThe ether solution is dried (MgSO4)

Sources & evidence

ORD record
ord-30fcdc137e5c47bbae32ef08adcaf413
Source dataset
uspto-grants-1978_12
Patent number
US04128560

Reaction notes

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