4-Benzylpiperidine → 5-[3-(4-Benzylpiperidin-1-yl)propoxy]-3,4-dihydroquinolin-2-ol

HRID 1979767Notes

Reaction equation

HRID 1979767 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10](=[O:16])[NH:11]2.[CH2:17]([CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[CH2:17]([CH:24]1[CH2:29][CH2:28][N:27]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:7]=2[CH2:8][CH2:9][C:10](=[O:16])[NH:11]3)[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 317384-BenzylpiperidineHCID 12899139HCID 12899139, compound

Product 1

HCID 30609865-[3-(4-Benzylpiperidin-1-yl)propoxy]-3,4-dihydroquinolin-2-olYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.8 Grams of 5-(3-chloropropoxy)-3,4-dihydrocarbostyril and 4.2 g of 4-benzylpiperidine were mixed with 40 ml of toluene and the mixture was heated under refluxing condition for 24 hours. After cooling of the reaction mixture, the precipitates thus formed were obtained by filtration and washed with water, then recrystallized from ethanol to obtain 6.3 g (yield: 76%) of 5-[3-(4-benzyl-1-piperidyl)propoxy]-3,4-dihydrocarbostyril as in the form of colorless needle-like crystals. Melting point: 143°-145° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder refluxing condition for 24 hours
  3. temperatureAfter cooling of the reaction mixture
  4. customthe precipitates thus
  5. customformed
  6. customwere obtained by filtration
  7. washwashed with water
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-df1eb848a9314d61974ac0baed8b88eb
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

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