1-Bromo-3-chloropropane → HCID 20570886, compound

HRID 1389243Notes

Reaction equation

HRID 1389243 reaction equation
[O:1]([CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][CH2:18][Cl:19].C(N(CC)CC)C>O1CCCC1>[O:1]([CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:16][CH2:17][CH2:18][Cl:19])[CH2:13][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 8471TriethylamineHCID 30174444-(Phenoxymethyl)piperidine

Product 1

HCID 20570886HCID 20570886, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 28.6 g (0.15 mole) of 4-phenoxymethyl-piperidine, 23.5 g (0.15 mole) of 1-bromo-3-chloropropane, 40.4 g (0.4 mole) of triethylamine and 150 ml of tetrahydrofuran is heated under reflux for 5 hours. After cooling, the reaction mixture is filtered, the filtrate is evaporated in a vacuum, the residue is extracted with diethyl ether and the extract is evaporated. There are obtained 33.6 g (84% of theory) of crude 3-(4-phenoxymethylpiperidino)-propyl chloride in the form of an oil which can be further used in this form. The pure compound is obtained by distillation and boils at 180°-183° C./0.4 mm Hg.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture is filtered
  5. customthe filtrate is evaporated in a vacuum
  6. extractionthe residue is extracted with diethyl ether
  7. customthe extract is evaporated

Sources & evidence

ORD record
ord-12a9528fd6684525b65e6eaedba3e153
Source dataset
uspto-grants-1981_01
Patent number
US04243807

Reaction notes

Loading…