Water → HCID 53392093, compound

HRID 1922335Notes

Reaction equation

HRID 1922335 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2].Cl.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 51117496-Nitro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 53392093HCID 53392093, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-nitro-3,4-dihydroquinolin-2(1H)-one (400 mg, 2.08 mmol), 1-(2-chloroethyl)piperidine hydrochloride(421 mg, 2.29 mmol) and potassium carbonate(862 mg, 6.24 mmol) in 10 mL DMF was stirred at room temperature overnight. After this time, the mixture was poured into 20 mL H2O then extracted with 2×50 mL CH2Cl2. The organic layer was separated, washed with brine and concentrated to give a yellow brown solid which was subjected to flash chromatography on silica gel using 5% MeOH/CH2Cl2 to give a yellow viscous oil (560 mg, 88.7%). 1H-NMR (CDCl3) δ: 8.14 (dd, J=2.7, 9 Hz, 1H), 8.06-8.05 (m, 1H), 7.24 (d, J=9.0 Hz, 1H), 4.11 (t, J=7.2 Hz, 2H), 3.02-2.95 (m, 2H), 2.73-2.67 (m, 2H), 2.57-2.48 (m, 6H), 1.59-1.44 (m, 6H).

Workup

  1. extractionthen extracted with 2×50 mL CH2Cl2
  2. customThe organic layer was separated
  3. washwashed with brine
  4. concentrationconcentrated
  5. customto give a yellow brown solid which

Sources & evidence

ORD record
ord-9b9dd011c36c4c2f85bbde2aa03cf7b9
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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