9-Methyl-3,9-diazabicyclo[3.3.1]nonane → 9-Methyl-3-(6-nitro-quinolin-2-yl)-3,9-diaza-bicyclo[3.3.1]Nonane

HRID 2246421Notes

Reaction equation

HRID 2246421 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH:3]1[CH2:4][NH:5][CH2:6]2.Cl[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=2)[N:13]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1>[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH:3]1[CH2:4][N:5]([C:12]1[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=3)[N:13]=1)[CH2:6]2

Participants

5

Reactant 3

HCID 189119-Methyl-3,9-diazabicyclo[3.3.1]nonaneHCID 81531DiisopropylethylamineHCID 109217232-Chloro-6-nitroquinoline

Product 1

HCID 247814269-Methyl-3-(6-nitro-quinolin-2-yl)-3,9-diaza-bicyclo[3.3.1]Nonane

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 9-methyl-3,9-diaza-bicyclo[3.3.1]nonane (0.50 g, 3.56 mmol), 2-chloro-6-nitroquinoline (0.74 g, 3.56 mmol), N,N-diisopropylethylamine (0.92 g, 7.13 mmol) and dioxane (25 ml) was stirred at reflux for 40 h. The mixture was allowed to cool to room temperature. The precipitated product was filtered and was washed with diethylether. The crude product was purified by silica gel column chromatography using a solvent mixture of dichloromethane, methanol and aqueous ammonia (9:1:1%). The pure product was isolated. Yield 300 mg (27%). Mp 166.2° C. LC-ESI-HRMS of [M+H]+ shows 313.1674 Da. Calc. 313.166451 Da, dev. 3 ppm.

Workup

  1. temperatureat reflux for 40 h
  2. filtrationThe precipitated product was filtered
  3. washwas washed with diethylether
  4. customThe crude product was purified by silica gel column chromatography
  5. additiona solvent mixture of dichloromethane, methanol and aqueous ammonia (9:1:1%)
  6. customThe pure product was isolated

Sources & evidence

ORD record
ord-f29174d76868480dade9530e8c2384a4
Source dataset
uspto-grants-2010_03
Patent number
US07687517B2

Reaction notes

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