Phosphorus pentachloride → 2-chloro-N-(2-chloroethyl)-N-methylbenzene ethanamine hydrochloride

HRID 358208Notes

Reaction equation

HRID 358208 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][N:16]([CH3:20])[CH2:17][CH2:18]O>C(Cl)Cl>[ClH:2].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][N:16]([CH2:17][CH2:18][Cl:2])[CH3:20]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 133669692-{[2-(2-Chlorophenyl)ethyl](methyl)amino}ethan-1-ol

Product 1

HCID 133924782-chloro-N-(2-chloroethyl)-N-methylbenzene ethanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 36 g. (0.173 mol) of phosphorous pentachloride in 300 ml. of methylene chloride was treated dropwise with a solution of 37 g. (0.173 mol) of the 2-[[2-(2-chlorophenyl)ethyl]methylamino]ethanol in 150 ml. of methylene chloride. After addition was complete, the mixture was refluxed overnight, evaporated to dryness and partitioned between dilute hydrochloric acid and ether. The aqueous layer was made basic with 10% sodium hydroxide and extracted well with ether. The ether extracts were washed with water and saturated sodium chloride, dried over magnesium sulfate and filtered. Addition of a saturated solution of ethereal hydrochloric acid gave a solid precipitate which was removed by filtration, washed with ether and dried to give 2-chloro-N-(2-chloroethyl)-N-methylbenzene ethanamine hydrochloride, m.p. 110°.

Workup

  1. additionA suspension of 36 g
  2. additionAfter addition
  3. temperaturethe mixture was refluxed overnight
  4. customevaporated to dryness
  5. custompartitioned between dilute hydrochloric acid and ether
  6. extractionextracted well with ether
  7. washThe ether extracts were washed with water and saturated sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. additionAddition of a saturated solution of ethereal hydrochloric acid
  11. customgave a solid precipitate which
  12. customwas removed by filtration
  13. washwashed with ether
  14. customdried

Sources & evidence

ORD record
ord-10ab9057414a4ef4a87a16bd2f3d190f
Source dataset
uspto-grants-1984_08
Patent number
US04465677

Reaction notes

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