4-Piperidinecarboxamide → 2-[2-(4-Carbamoylpiperidino)ethoxy]bibenzyl

HRID 27058

Reaction equation

HRID 27058 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH:19]1[CH2:24][CH2:23][CH:22]([C:25]([NH2:27])=[O:26])[CH2:21][CH2:20]1>O1CCCC1.O>[C:25]([CH:22]1[CH2:23][CH2:24][N:19]([CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:20][CH2:21]1)(=[O:26])[NH2:27]

Participants

5

Reactant 2

HCID 37724-PiperidinecarboxamideHCID 205450162-(2-Bromoethoxy)bibenzyl

Product 1

HCID 128525822-[2-(4-Carbamoylpiperidino)ethoxy]bibenzylYield 82.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2 g of 2-(2-bromoethoxy)bibenzyl and 1.7 g of 4-piperidinecarboxamide in 20 ml of tetrahydrofuran and 10 ml of water was stirred at 70° C. for 10 hours. The reaction mixture was concentrated and to the residue was added 1 N NaOH aqueous solution. The resultant crystals were filtered, washed well with water and then recrystallized from ethanol to give 1.9 g (82% yield) of 2-[2-(4-carbamoylpiperidino)ethoxy]bibenzyl, m. p. 60°-63° C.

Workup

  1. concentrationThe reaction mixture was concentrated and to the residue
  2. additionwas added 1 N NaOH aqueous solution
  3. filtrationThe resultant crystals were filtered
  4. washwashed well with water
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e92d68471f384dd693101c367d0b9ebe
Source dataset
uspto-grants-1980_09
Patent number
US04220603

Linked notes

Loading…