Hydrochloric Acid → 4-(2-Chloroethyl)morpholine

HRID 247139Notes

Reaction equation

HRID 247139 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[OH-].[Na+].Cl.[OH-]>C1(C)C=CC=CC=1.O>[Cl:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 961HydroxideHCID 14798Sodium HydroxideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 767274-(2-Chloroethyl)morpholine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of N-chloroethyl morpholine in toluene was prepared in the following manner. 930.4 grams of N-chloroethyl morpholine hydrochloride (5 moles) available commercially from Aldrich Chemical Co. was dissolved in 500 milliliters water. A solution of 300.0 grams of sodium hydroxide in 300 milliliters water was slowly added to the hydrochloride solution keeping the temperature below 35° C. during addition. After all the hydroxide solution had been added, the reaction was allowed to stir at room temperature for five minutes and then transferred to a separatory funnel. The upper layer was separated and the bottom layer was washed with 500 milliliters toluene. The combined organic layers were dried with anhydrous potassium carbonate, filtered and added in a slow stream to the refluxing alkoxide solution prepared above. After addition the reaction was refluxed overnight.

Workup

  1. customthe temperature below 35° C.
  2. additionduring addition
  3. customtransferred to a separatory funnel
  4. customThe upper layer was separated
  5. washthe bottom layer was washed with 500 milliliters toluene
  6. dry with materialThe combined organic layers were dried with anhydrous potassium carbonate
  7. filtrationfiltered
  8. additionadded in a slow stream to the refluxing alkoxide solution
  9. customprepared above
  10. additionAfter addition the reaction
  11. temperaturewas refluxed overnight

Sources & evidence

ORD record
ord-12ccff90f9744236979b123c159ef341
Source dataset
uspto-grants-1987_11
Patent number
US04705840

Reaction notes

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