Hydrochloric Acid → 1-[2-(Benzofurazan-5-yl)ethyl]-4-piperidinone

HRID 1591206노트

반응식

HRID 1591206 반응식
[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][N:12]3[CH2:21][CH2:20][C:15]4(OCC[O:16]4)[CH2:14][CH2:13]3)[CH:8]=[CH:9][C:2]=12.Cl.[OH-].[Na+]>>[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][N:12]3[CH2:21][CH2:20][C:15](=[O:16])[CH2:14][CH2:13]3)[CH:8]=[CH:9][C:2]=12

참가 물질

4

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 190452468-[2-(Benzofurazan-5-yl)ethyl]1,4-dioxa-8-aza spiro[4.5]decane

생성물 1

HCID 190452521-[2-(Benzofurazan-5-yl)ethyl]-4-piperidinone수율 88%

실험 절차

A solution of 8-[2-(benzofurazan-5-yl)ethyl]-1,4-dioxa-8-aza spiro[4.5]decane (20.0 g, 69.1 mmol) in 1N aqueous HCl (200 mL, 200 mmol) was heated to reflux for 1.5 hr. The cooled solution was adjusted to pH 8.5 with 40% aqueous sodium hydroxide and extracted with ethyl acetate (250 mL then 100 mL). The combined extracts were washed twice with 1N aqueous HCl (200 mL combined). The acid layers were heated to reflux for 1 hr and then cooled. Basification as above, extraction into ethyl acetate, drying (Na2SO4), concentration, and trituration with hexanes afforded 1-[2-(benzofurazan-5-yl)ethyl]piperidin-4-one as a solid 14.9 g (88%). HPLC: Rt=3.0 min, 90:10 (0.1% H3PO4 in water: acetonitrile) flow=2.0 mL/min, Waters C18 micro bondapak 25 cmL.

후처리

  1. temperatureto reflux for 1.5 hr
  2. extractionextracted with ethyl acetate (250 mL
  3. washThe combined extracts were washed twice with 1N aqueous HCl (200 mL combined)
  4. temperatureThe acid layers were heated
  5. temperatureto reflux for 1 hr
  6. temperaturecooled
  7. extractionBasification as above, extraction into ethyl acetate
  8. customdrying
  9. concentration(Na2SO4), concentration, and trituration with hexanes

출처 및 근거

ORD 기록
ord-bb106d77ab854ffdb5213c56c2b85f7a
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05206240

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