Triethylamine → Cyclohexane n-[1,1-dimethyl-2-(3-nitro-7-phenylquinolin-4-ylamino)ethyl]carboxamide

HRID 9408

Reaction equation

HRID 9408 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]([CH3:19])([NH2:18])[CH3:17])=[CH:11][CH:10]=[C:9]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:8]=2)([O-:3])=[O:2].C(N(CC)CC)C.[CH:33]1([C:39](Cl)=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>ClCCl>[CH3:17][C:16]([NH:18][CH:39]=[O:40])([CH3:19])[CH2:15][NH:14][C:13]1[C:12]2[C:7](=[CH:8][C:9]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2].[CH2:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 86593761N1-(3-nitro-7-phenylquinolin-4-yl)-2-methylpropane-1,2-diamine

Product 1

HCID 87586912Cyclohexane n-[1,1-dimethyl-2-(3-nitro-7-phenylquinolin-4-ylamino)ethyl]carboxamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N1-(3-nitro-7-phenylquinolin-4-yl)-2-methylpropane-1,2-diamine (3.56 g, 10.6 mmol) in dichloromethane (100 mL) was cooled to 0° C. Triethylamine (3.0 mL, 21 mmol) and cyclohexanecarbonyl chloride (1.55 mL, 11.6 mmol) were sequentially added. The reaction was allowed to warm to ambient temperature and stirred for two hours. The reaction was washed sequentially with water (2×100 mL) and brine (100 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 65:35 hexanes:ethyl acetate) to provide 3.33 g of cyclohexane N-[1,1-dimethyl-2-(3-nitro-7-phenylquinolin-4-ylamino)ethyl]carboxamide as a yellow solid.

Workup

  1. washThe reaction was washed sequentially with water (2×100 mL) and brine (100 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel (eluting with 65:35 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-f15ea28ffbee4c82a8f9b5a3dcec7661
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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