Acetyl chloride → Ammonia

HRID 2119372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2119372
[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-1-piperazinyl]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-2,6-dimethyl-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-f63a1ac35cc24afaa1655299a88cc552
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06686357B1

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