Water → 3-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)quinolin-2(1H)-one

HRID 550387Notes

Reaction equation

HRID 550387 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[C:16](Cl)=[N:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:26]>Cl>[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([C:15]2[C:16](=[O:26])[NH:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 184442481-Benzyl-4-(2-chloroquinolin-3-yl)piperidin-4-ol

Product 1

HCID 184442473-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)quinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-(1-Benzyl-4-hydroxypiperidin-4-yl)-2-chloroquinoline (11.0 g, 31.1 mmol) was refluxed in 6 N hydrochloric acid for 8 h. The solution was cooled and water (100 mL) added. The precipitated solid was collected and dried to give the title compound, 7.9 g. MS: m/z=317 (M+1). 1H NMR (500 MHz, CD3OD) δ 7.97 (s, 1H), 7.70 (d, J=7 Hz, 1H), 7.60 (m, 2H), 7.55 (m, 4H), 7.35 (d, J=9 Hz, 1H), 7.27 (t, J=8 Hz, 1H), 6.50 (m, 1H), 4.49 (ABq, J=13 Hz, Δν=16 Hz, 2H), 3.92 (m, 2H), 3.76 (dt, J=12.4 Hz, 1H), 3.40 (m, 1H), 2.96 (m, 2H).

Workup

  1. temperatureThe solution was cooled
  2. customThe precipitated solid was collected
  3. customdried

Sources & evidence

ORD record
ord-bbff09f3275d496eb8d98c1ac8f6538e
Source dataset
uspto-grants-2011_05
Patent number
US07947678B2

Reaction notes

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