Dipropylamine → 4-(N,N-Dipropyl)amino-2-methyl-10-(2,4,6-trimethylphenyl)-pyrido[2,3-b]indolizine

HRID 2299264Notes

Reaction equation

HRID 2299264 reaction equation
Cl[C:2]1[C:14]2[N:13]3[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]3)=[C:7]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:6]=2[N:5]=[C:4]([CH3:24])[CH:3]=1.[CH2:25]([NH:28][CH2:29][CH2:30][CH3:31])[CH2:26][CH3:27]>CS(C)=O.O>[CH2:25]([N:28]([C:2]1[C:14]2[N:13]3[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]3)=[C:7]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:6]=2[N:5]=[C:4]([CH3:24])[CH:3]=1)[CH2:29][CH2:30][CH3:31])[CH2:26][CH3:27]

Participants

5

Reactant 2

HCID 8902DipropylamineHCID 155132734-Chloro-2-methyl-10-(2,4,6-trimethylphenyl)pyrido[2,3-b]indolizine

Product 1

HCID 99308234-(N,N-Dipropyl)amino-2-methyl-10-(2,4,6-trimethylphenyl)-pyrido[2,3-b]indolizineYield 87%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-chloro-2-methyl-10-(2,4,6-trimethylphenyl)pyrido[2,3-b]indolizine (10.0 g; 30 mmol) and dipropylamine (15 mL; 1 mol) in DMSO (30 mL) is heated at 130° C. under nitrogen atmosphere for two days. The mixture is cooled to room temperature, diluted with water (ca. 300 mL), and extracted with ether (100 mL×2). The combined organics are washed successively with saturated ammonium chloride and saturated brine, dried (Na2SO4), filtered, and concentrated. The concentrate is chromatographed (first with 5% ethyl acetate in hexane and then with 10% triethylamine in hexane) to give 10.4 g of the title compound (compound 1, Table 1) as a fluorescent yellow foam (87%): 1H nmr (400 MHz, CDCl3) d 0.90 (t, 6 H), 1.6 (br, 4 H), 2.02 (s, 6 H), 2.37 (s, 3 H), 2.62 (s, 3 H), 3.2 (br, 4 H), 6.52 (t, 1 H), 6.73 (s, 1 H), 6.89 (t, 1 H), 7.00 (s, 2 H), 7.06 (d, 1 H), 8.98 (d, 1 H).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted with ether (100 mL×2)
  3. washThe combined organics are washed successively with saturated ammonium chloride and saturated brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate is chromatographed (first with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c901cb24586f43598fb8d4a40346e814
Source dataset
uspto-grants-2002_12
Patent number
US06495686B2

Reaction notes

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