Toluene → N-[2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)ethyl]-N-(2-chloroethyl)-N-methylamine hydrochloride

HRID 248838Notes

Reaction equation

HRID 248838 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@@H:5]([CH:8]([CH3:10])[CH3:9])[C@H:4]([O:11][CH2:12][CH2:13][N:14]([CH2:16][CH2:17]O)[CH3:15])[CH2:3]1.S(Cl)([Cl:21])=O.C1(C)C=CC=CC=1>ClCCl.CN(C)C=O>[ClH:21].[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@@H:5]([CH:8]([CH3:10])[CH3:9])[C@H:4]([O:11][CH2:12][CH2:13][N:14]([CH2:16][CH2:17][Cl:21])[CH3:15])[CH2:3]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 18651837HCID 18651837, compound

Product 1

HCID 67883408N-[2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)ethyl]-N-(2-chloroethyl)-N-methylamine hydrochlorideYield 97.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

19 g of N-[2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)ethyl]-N-(2-hydro xyethyl)-N-methylamine were dissolved in 200 ml of dichloromethane. 17.6 g of thionyl chloride were then added dropwise to the solution with ice-cooling. Two drops of dimethylformamide were then added as a catalyst, and the solution was heated under reflux for 3 hours. The reaction mixture was worked up by adding toluene and then evaporating the solution, after which fresh toluene was added to the residue and evaporated two more times. The remaining residue was then dissolved in dichloromethane, and ether was added dropwise to the solution to precipitate the reaction product. The resulting precipitate was filtered out and dried. 22.5 g of N-[2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)ethyl]-N-(2-chloroethyl)-N-methylamine hydrochloride having a melting point of 184° C.-194° C. were obtained.

Workup

  1. temperaturecooling
  2. temperaturethe solution was heated
  3. temperatureunder reflux for 3 hours
  4. customevaporating the solution
  5. additionafter which fresh toluene was added to the residue
  6. customevaporated two more times
  7. dissolutionThe remaining residue was then dissolved in dichloromethane
  8. additionether was added dropwise to the solution
  9. customto precipitate the reaction product
  10. filtrationThe resulting precipitate was filtered out
  11. customdried

Sources & evidence

ORD record
ord-41396bde195d48549c4ebd1283135de0
Source dataset
uspto-grants-1993_05
Patent number
US05212173

Reaction notes

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