Triethylamine → 1-[(3-Nitroquinolin-4-ylamino)methyl]cyclohexanol

HRID 44791

Reaction equation

HRID 44791 reaction equation
Cl.[NH2:2][CH2:3][C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.Cl[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23].C(N(CC)CC)C.[N+](C1C=NC2C(C=1O)=CC=CC=2)([O-])=O>ClCCl.Cl.NCC1(O)CCCCC1>[N+:22]([C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:12]=1[NH:2][CH2:3][C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[CH:20][CH:19]=[CH:18][CH:17]=2)([O-:24])=[O:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)HCID 112758084-Chloro-3-nitroquinoline3×HCID 178526762HCID 178526762, compound

Product 1

HCID 574578081-[(3-Nitroquinolin-4-ylamino)methyl]cyclohexanolYield 105.3%

Reagents, catalysts & solvents 2

HCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)CatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 1-aminomethyl-1-cyclohexanol hydrochloride (20.0 g, 121 mmol) and 4-chloro-3-nitroquinoline (24.0 g, 115 mmol) in dichloromethane (550 mL) was cooled to 0° C., and triethylamine (40 mL, 290 mmol) was added dropwise over a period of 30 minutes. The reaction was allowed to warm to room temperature over two hours. An analysis by HPLC indicated that the 4-chloro-3-nitroquinoline starting material actually contained some 3-nitroquinolin-4-ol, and additional pure 4-chloro-3-nitroquinoline (12.0 g, 57.5 mmol) was added. The reaction was stirred for four hours, and additional 1-aminomethyl-1-cyclohexanol hydrochloride (2.0 g, 12 mmol) was added, and the resulting suspension was stirred for three days. The solvent was removed under reduced pressure, and the residue was triturated in water for one hour and isolated by filtration. The resulting solid was triturated with hot dichloromethane and isolated by filtration from the hot mixture to provide 36.5 g of 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclohexanol as a bright yellow powder.

Workup

  1. temperatureto warm to room temperature over two hours
  2. additionwas added
  3. stirringthe resulting suspension was stirred for three days
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was triturated in water for one hour
  6. customisolated by filtration
  7. customThe resulting solid was triturated with hot dichloromethane
  8. customisolated by filtration from the hot mixture

Sources & evidence

ORD record
ord-8dac8ca5e7f441478899ab7695f6fb65
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Linked notes

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