Triethylamine → 1-(1-Boc-4-piperidyl)-4-phenyl-3,1-benzoxazin-2-one

HRID 1377698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1377698
[C:1]1([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C>C1COCC1>[C:22]([N:19]1[CH2:20][CH2:21][CH:16]([N:15]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:8][C:30]2=[O:32])[CH2:17][CH2:18]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 57083091phenyl-(2-(1-Boc-4-piperidinylamino)phenyl) carbinol

Produkt 1

HCID 229146691-(1-Boc-4-piperidyl)-4-phenyl-3,1-benzoxazin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Phenyl-(2-(1-Boc-4-piperidinylamino)phenyl) carbinol from Step 2 above (1.8 g, 4.7 mmol) was stirred in dry THF in an ice bath under nitrogen, and triphosgene (0.47 g, 1.57 mmol) was added followed by triethylamine (1.96 mL, 1.42 g, 14.1 mmol). The ice bath was removed and the mixture was stirred at ambient temperature for 18 hours. Water was added, and the mixture was extracted with ethyl acetate. The combined ethyl acetate fractions were washed with 1N HCl followed by saturated sodium bicarbonate, dried over sodium sulfate, filtered, and evaporated to dryness in vacuo to give 1-(1-Boc-4-piperidyl)-4-phenyl-3,1-benzoxazin-2-one.

Aufarbeitung

  1. customThe ice bath was removed
  2. additionWater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined ethyl acetate fractions were washed with 1N HCl
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9d66df4f5c6c4727b2ff08d02e8b5f85
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05665719

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