Toluene → HCID 1770823, compound

HRID 517868Notes

Reaction equation

HRID 517868 reaction equation
[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.C1(C)C=CC=CC=1.[C:23](#[N:26])[CH:24]=[CH2:25]>C1C=CC=CC=1>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6]([CH2:25][CH2:24][C:23]#[N:26])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7855Acrylonitrile2×HCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-

Product 1

HCID 1770823HCID 1770823, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (1.5 g, 7.5 mmol) was taken in 20 ml of benzene: toluene mixture (1:1) along with acrylonitrile (1 ml, 15 mmol), cooled to 0° C., followed by addition of triton base (0.3 ml). The contents were stirred for 15 min. Acrylonitrile and triton base (same amount) were added and stirred at RT for 1 h. The reaction was monitored by TLC and LCMS. On completion of the reaction, reaction mixture was quenched with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain solid material, which was crystallized using diethyl ether to yield 3-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)propanenitrile (yield: 1 g). 1H NMR (CDCl3) 7.25 (s, 1H), 7.18-7.15 (d, 1H), 7.08-7.03 (d, 1H), 4.38-4.32 (t, 2H), 3.70-3.65 (m, 2H), 2.95-2.90 (m, 4H), 2.78-2.70 (t, 2H), 2.58 (s, 3H), 2.45 (s, 3H).

Workup

  1. stirringstirred at RT for 1 h
  2. customOn completion of the reaction, reaction mixture
  3. customwas quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customto obtain solid material, which
  8. customwas crystallized

Sources & evidence

ORD record
ord-b157316e3fd54db783e0653532d8abf3
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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