Water → HCID 68595185, compound

HRID 517869Notes

Reaction equation

HRID 517869 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.[C:16](#[N:19])[CH:17]=[CH2:18].O>C1C=CC=CC=1.C1(C)C=CC=CC=1.CO.ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:18][CH2:17][C:16]#[N:19])[C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 7855AcrylonitrileHCID 196158-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indole

Product 1

HCID 68595185HCID 68595185, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 1140TolueneSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
0 °C

Procedure

8-chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (1.00 g, 4.5 mmol) was stirred in benzene (15 mL) and toluene (20 mL). To this solution acrylonitrile (0.5 mL, 7.5 mmol) was added. The resulting reaction mixture was stirred at 0° C. for 10 minutes. Ice cold solution of 1 ml of Triton-B® was added to it. The reaction mixture was again stirred at room temperature for 4 h. The reaction was monitored by TLC in 10% Methanol-dichloromethane. Water was added to the reaction mixture and extracted organic layer was given water wash (3 times). The organic layer was then concentrated and purified by silica gel (100-200 mesh) chromatography using 0-10% methanol:dichloromethane as eluent. The obtained 3-(8-chloro-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)propanenitrile was converted into its oxalate salt. 1H NMR (DMSO) 7.65 (d, 1H), 7.55 (s, 1H), 7.20 (d, 1H), 4.50 (t, 2H), 4.30 (m, 2H), 3.40 (m, 2H), 3.20 (m, 2H), 3.0 (t, 2H), 2.90 (s, 3H).

Workup

  1. customThe resulting reaction mixture
  2. additionIce cold solution of 1 ml of Triton-B® was added to it
  3. stirringThe reaction mixture was again stirred at room temperature for 4 h
  4. extractionextracted organic layer
  5. washwash (3 times)
  6. concentrationThe organic layer was then concentrated
  7. custompurified by silica gel (100-200 mesh) chromatography

Sources & evidence

ORD record
ord-a8ab8d3f0277484bb84ee49f2e0f74ee
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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