Triethylamine → HCID 67519506, compound

HRID 1925471Notes

Reaction equation

HRID 1925471 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20].Cl.[O:23]1[CH2:28][CH2:27][CH:26]([CH2:29][NH2:30])[CH2:25][CH2:24]1>C1COCC1>[N+:19]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:9]=1[NH:30][CH2:29][CH:26]1[CH2:27][CH2:28][O:23][CH2:24][CH2:25]1)=[CH:17][CH:16]=[CH:15][CH:14]=2)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 44118690(Oxan-4-yl)methanamine hydrochloride

Product 1

HCID 67519506HCID 67519506, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere THF (90 mL) and triethylamine (17.5 mL, 125.6 mmol) were added sequentially to a mixture of crude 4-chloro-3-nitroquinoline (13.10 g, 62.81 mmol) and 1-tetrahydro-2H-pyran-4-ylmethylamine hydrochloride (10.0 g, 65.95 mmol). The reaction mixture was placed in an oil bath at 45° C. for 1 hour and then concentrated under reduced pressure. The residue was diluted with THF (30 mL) and water (200 mL). The THF was removed under reduced pressure. A solid was isolated by filtration and dried to provide 16.10 g of 3-nitro-N-(tetrahydro-2H-pyran-4-ylmethyl)quinolin-4-amine as a light yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with THF (30 mL) and water (200 mL)
  3. customThe THF was removed under reduced pressure
  4. customA solid was isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-66726fa021194d05a1c086a08e858f28
Source dataset
uspto-grants-2012_05
Patent number
US08178677B2

Reaction notes

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