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Hydrochloric Acid → (3R)-3-(3,4-dimethylbenzyl)-1-[4-(3,3-dimethylmorpholino)-2-butynyl]piperazine trihydrochloride

HRID 584204
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 584204
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]#[C:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][C:20]2([CH3:26])[CH3:25])[CH2:11][C@H:10]1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([CH3:35])[CH:29]=1)=O)(C)(C)C>C(OCC)(=O)C.C(O)C>[ClH:1].[ClH:1].[ClH:1].[CH3:35][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][C:31]=1[CH3:34])[CH2:27][C@H:10]1[NH:9][CH2:14][CH2:13][N:12]([CH2:15][C:16]#[C:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][C:20]2([CH3:26])[CH3:25])[CH2:11]1
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Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 53964510(2R)-1-tert-butoxycarbonyl-2-(3,4-dimethylbenzyl)-4-[4-(3,3-dimethylmorpholino)-2-butynyl]-piperazine

Produkt 1

HCID 69677662(3R)-3-(3,4-dimethylbenzyl)-1-[4-(3,3-dimethylmorpholino)-2-butynyl]piperazine trihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

A solution of 4N hydrogen chloride in ethyl acetate was added to a solution of (2R)-1-tert-butoxycarbonyl-2-(3,4-dimethylbenzyl)-4-[4-(3,3-dimethylmorpholino)-2-butynyl]piperazine (40.0 g) in ethanol (120 ml) at room temperature and the whole was stirred for 12 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (500 ml) and potassium carbonate solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (300 ml). The combined extract was dried over sodium sulfate and evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel using a mixed solvent of n-hexane and ethyl acetate (3:1). The fractions containing the objective compound were collected and evaporated under reduced pressure, and treated with 4N hydrogen chloride in ethyl acetate to give (3R)-3-(3,4-dimethylbenzyl)-1-[4-(3,3-dimethylmorpholino)-2-butynyl]piperazine trihydrochloride (37.7 g).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (500 ml) and potassium carbonate solution
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (300 ml)
  5. extractionThe combined extract
  6. dry with materialwas dried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel using a mixed solvent of n-hexane and ethyl acetate (3:1)
  9. additionThe fractions containing the objective compound
  10. customwere collected
  11. customevaporated under reduced pressure
  12. additiontreated with 4N hydrogen chloride in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2c056dfc3df541f3a819893966c006fe
Quelldatensatz
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06924278B2

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