Hydrochloric Acid → 1'-Benzyl-5-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]

HRID 270092

반응식

HRID 270092 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=3[C:15](=O)[O:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=3[CH2:15][O:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 598336431'-benzyl-5-chloro-3H-spiro[isobenzofuran-1,4'-piperidin]-3-one

생성물 1

HCID 598336321'-Benzyl-5-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]수율 95.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a solution of 1′-benzyl-5-chloro-3H-spiro[2-benzofuran-1,4′-piperidin]-3-one (1.1 g, 3.35 mmol) in THF (12 mL) was added 1 M solution of borane complex in THF (7 mL, 7.0 mmol) slowly at 0° C. After addition was complete reaction mixture was kept at room temperature for 30 min, then kept at reflux overnight, cooled to 0° C. and 6M aqueous HCl (3.5 mL) was added slowly. The reaction mixture was kept at reflux for 5 h, cooled to 0° C., pH of the reaction mixture was adjusted to 10 by addition of aqueous NaOH (6M) and the whole was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulphate (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by silica gel flash chromatography (0-30% ethyl acetate in petroleum ether) to give the subtitled compound (1.0 g).

후처리

  1. additionAfter addition
  2. temperatureat reflux overnight
  3. temperatureat reflux for 5 h
  4. temperaturecooled to 0° C.
  5. extractionthe whole was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over sodium sulphate (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel flash chromatography (0-30% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-4fa3fb46812240c59a78ebdd85624430
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

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