Hydrochloric Acid → 1-[2-Chloro-3-(1,1-dimethylethoxy)propyl]pyrrolidine

HRID 4508

Reaktionsgleichung

Reaktionsgleichung von HRID 4508
P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:7][C:8]([CH3:20])([O:10][CH2:11][CH:12](O)[CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH3:9].[ClH:21]>C1(C)C=CC=CC=1.O1CCCC1>[Cl:21][CH:12]([CH2:11][O:10][C:8]([CH3:20])([CH3:9])[CH3:7])[CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 24819Phosphorus pentachlorideHCID 140970901-[3-(1,1-Dimethylethoxy)-2-hydroxypropyl]pyrrolidine

Produkt 1

HCID 201310931-[2-Chloro-3-(1,1-dimethylethoxy)propyl]pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred, cooled suspension of 34.7 g (0.167 ml) of phosphorous pentachloride in 20 ml of dry toluene (argon atmosphere) was added a solution of 31.93 g (0.159 m) of 1-[3-(1,1-dimethylethoxy)-2-hydroxypropyl]pyrrolidine (the product of Example 13a) and excess hydrogen chloride (gas) in 46 ml of dry toluene and 50 ml of dry tetrahydrofuran at a rate to keep the reaction temperature at 10°-25° C. When the addition was completed, the cooling bath was removed and the reaction mixture was stirred at ambient temperature for 1.5 hr. The reaction mixture was added portionwise, with stirring to a cooled solution of 122 ml of 45% potassium hydroxide and 230 g of ice at a rate to keep the reaction temperature at 25°-35° C. The reaction mixture was partitioned between ether and water. The ether portion was dried and concentrated in vacuo to give 31.69 g of oily title compound.

Aufarbeitung

  1. temperatureTo a stirred, cooled
  2. customat 10°-25° C
  3. additionWhen the addition
  4. customthe cooling bath was removed
  5. additionThe reaction mixture was added portionwise
  6. stirringwith stirring to a cooled solution of 122 ml of 45% potassium hydroxide and 230 g of ice at a rate
  7. customat 25°-35° C
  8. customThe reaction mixture was partitioned between ether and water
  9. dry with materialThe ether portion was dried
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-241aa2d333114c3fb4a89c919eca50fd
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727072

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