N-4-Piperidylbenzamide → HCID 21411739, compound

HRID 2071612Notes

Reaction equation

HRID 2071612 reaction equation
Cl[C:2]1[C:11]([CH3:13])([CH3:12])[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([OH:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:21]([NH:29]C1CCNCC1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1.C(N(CC)CC)C>[OH:14][C:10]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([N:3]2[CH2:4][CH2:9][CH:10]([C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:21]([NH2:29])=[O:28])[CH2:11][CH2:2]2)[C:11]1([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 118120N-4-PiperidylbenzamideHCID 214117332-Chloro-3,3-dimethyl-4-phenyl-3,4-dihydro-4-quinolinol

Product 1

HCID 21411739HCID 21411739, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-3,4-dihydro-3,3-dimethyl-4-phenylquinolin-4-ol (1.0g., 0.0035 mole) in dry dioxan (15 ml.) and triethylamine (1 ml.) was added 4-benzamidopiperidine (0.67 g., 0.0035 mole). After heating at 80° C for 41/2 hours, the reaction mixture was cooled, a small amount of solid was filtered off and the filtrate evaporated down to a residue. Trituration with hexane yielded the title compound as the crude free base (m.p. 78° - 81° C). The hydrobromide (1.05g., m.p. 166° - 168° C) was obtained as the monohydrate on crystallisation from isopropyl alcohol. [Found: C, 62.75; H, 6.2; N, 7.3% C29H31N3O2H2O HBr requires: C, 63.0; H, 6.2; N, 7.6%].

Workup

  1. temperaturethe reaction mixture was cooled
  2. filtrationa small amount of solid was filtered off
  3. customthe filtrate evaporated down to a residue

Sources & evidence

ORD record
ord-81195f34b8be462e9fa3583f69c0667c
Source dataset
uspto-grants-1977_09
Patent number
US04048177

Reaction notes

Loading…