HCID 86742466, compound → HCID 86742465, compound

HRID 867614Notes

Reaction equation

HRID 867614 reaction equation
[ClH:1].[CH2:2]([N:4]([CH2:9][CH3:10])[C@@H:5]([CH3:8])[CH2:6]O)[CH3:3]>S(Cl)(Cl)=O>[ClH:1].[CH2:2]([N:4]([CH2:9][CH3:10])[C@@H:5]([CH3:8])[CH2:6][Cl:1])[CH3:3]

Participants

3

Reactant 1

HCID 86742466HCID 86742466, compound

Product 1

HCID 86742465HCID 86742465, compoundYield 164.3%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

(S)-2-Diethylaminopropanol hydrochloride (50 g) is added in small portions to thionyl chloride (110 cc) at 2° C. The solution obtained is then heated to 60° C. for 4 hours. Excess thionyl chloride is removed by distillation under reduced pressure (90 kPa) and ethyl ether (250 cc) is then added to the residue obtained. The resultant solid is filtered off, is rinsed with ethyl ether (300 cc) and is then recrystallized from methyl isobutyl ketone (150 cc). After filtration and washing with ethyl ether, (S)-2-diethylamino-1-chloropropane hydrochloride (45.6 g) is obtained in the form of white crystals melting at 103° C., [α]D20 =0 (c=0.7; ethanol).

Workup

  1. customThe solution obtained
  2. customExcess thionyl chloride is removed by distillation under reduced pressure (90 kPa) and ethyl ether (250 cc)
  3. additionis then added to the residue
  4. customobtained
  5. filtrationThe resultant solid is filtered off
  6. washis rinsed with ethyl ether (300 cc)
  7. customis then recrystallized from methyl isobutyl ketone (150 cc)
  8. filtrationAfter filtration
  9. washwashing with ethyl ether

Sources & evidence

ORD record
ord-8e2ab71bb5b84af4a3730e565978cd33
Source dataset
uspto-grants-1988_10
Patent number
US04775753

Reaction notes

Loading…