Acetyl chloride → Ammonia

HRID 1635629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1635629
[C:1](Cl)(=[O:3])[CH3:2].[O:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]1[C:20]([NH:22][CH2:23][CH2:24][N:25]1[C@H:30]([CH3:31])[CH2:29][NH:28][CH2:27][C@@H:26]1[CH3:32])=[O:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH3:7].[C:1]([N:28]1[CH2:27][C@@H:26]([CH3:32])[N:25]([CH2:24][CH2:23][NH:22][C:20]([C@@H:15]2[CH2:16][CH2:17][CH2:18][CH2:19][N:14]2[C:6]2[O:5][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[N:7]=2)=[O:21])[C@@H:30]([CH3:31])[CH2:29]1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 9821522(2S)-1-(1,3-benzoxazol-2-yl)-N2-2-[(cis)-2,6-dimethyl-1-piperazinyl]ethyl-2-piperidinecarboxamide

Produkt 2

HCID 222AmmoniaHCID 9954262(2S)-N2-2-[(cis)-4-acetyl-2,6-dimethyl-1-piperazinyl]ethyl-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Acetyl chloride (0.018 ml) was added to a solution of (2S)-1-(1,3-benzoxazol-2-yl)-N2-2-[(cis)-2,6-dimethyl-1piperazinyl]ethyl-2-piperidinecarboxamide (0.1 g) [see Example 8] and potassium carbonate (36 mg) in acetonitrile (2 ml). The reaction mixture was stirred at room temperature for 2 hours, after which time the solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 97:3.5:0.5 changing to 97:3:1, by volume, dichloromethane:methanol:0.88 aqueous ammonia solution (93:7:1), to afford (2S)-N2-2-[(cis)-4-acetyl-2,6dimethyl-1-piperazinyl]ethyl-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide (91.6 mg) as a white foam.

Aufarbeitung

  1. customafter which time the solvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 97:3.5:0.5 changing to 97:3:1, by volume, dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-18de1e3e799142ef883ef4aa86e7220c
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06509464B1

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