Triethylamine → HCID 10899796, compound

HRID 1410548Notes

Reaction equation

HRID 1410548 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.O.Cl.[NH:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1.C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 2723901Piperonylamine

Product 1

HCID 10899796HCID 10899796, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

64.00 g (0.443 mol) of o-fluorobenzylchloride was weighed, to which 250 mL of dichloromethane was added. 62.40 g (0.406 mol) of 4-piperidone hydrochloride monohydrate was added under stirring, and then 91.00 g (0.899 mol) of triethylamine was added dropwise under cold water cooling and stirring. The reaction was stirred at room temperature for 4.5 h, and then stirred under reflux and reacted overnight. On the next day, the reaction was cooled, filtered to remove solid, washed in sequence with dichloromethane and ethyl ether, combined, washed with water and dried, and the solvent was recovered to obtain 68.95 g crude product (82.00%), which was used directly in the next reaction.

Workup

  1. additionwas added
  2. stirringstirring
  3. stirringThe reaction was stirred at room temperature for 4.5 h
  4. stirringstirred
  5. temperatureunder reflux
  6. customreacted overnight
  7. temperatureOn the next day, the reaction was cooled
  8. filtrationfiltered
  9. customto remove solid
  10. washwashed in sequence with dichloromethane and ethyl ether
  11. washwashed with water
  12. customdried
  13. customthe solvent was recovered

Sources & evidence

ORD record
ord-f98bbc9cac0f44a7aceebe3694228a7f
Source dataset
uspto-grants-2014_12
Patent number
US08921563B2

Reaction notes

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