Triethylamine → HCID 11959582, compound

HRID 1410551Notes

Reaction equation

HRID 1410551 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4]Br.O.Cl.[NH:13]1[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]1.C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][N:13]1[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 2723901Piperonylamine

Product 1

HCID 11959582HCID 11959582, compoundYield 217%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

28.20 g (0.125 mol) of 2,4-difluorobenzyl bromide was weighed, to which 200 mL of dichloromethane was added and then 62.00 g (0.404 mol) of 4-piperidone hydrochloride monohydrate was added under stirring. And then 86.00 g (0.850 mol) of triethylamine was added dropwise at a bath temperature of 30-40° C. under stirring. After the addition, the reaction was heated, refluxed and reacted overnight. On the next day, the reaction was cooled, filtered to removed solid, washed in sequence with dichloromethane and ethyl ether, combined, washed with water and dried, and the solvent was recovered to obtain 61.10 g of crude product (73.3%), 1H-NMR (CDCl3, ppm) δ: 7.31-7.33 (5H, m), 3.56 (2H, s), 2.64 (2H, s), 2.53-2.62 (4H, m), 1.52-1.86 (4H, m); which was used directly in the next step of reaction.

Workup

  1. additionwas added
  2. stirringunder stirring
  3. additionAfter the addition
  4. temperaturethe reaction was heated
  5. temperaturerefluxed
  6. customreacted overnight
  7. temperatureOn the next day, the reaction was cooled
  8. filtrationfiltered
  9. customto removed 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-454d2e49699641878ddcb348afc90d69
Source dataset
uspto-grants-2014_12
Patent number
US08921563B2

Reaction notes

Loading…