Potassium Hydroxide → Ammonia

HRID 500630노트

반응식

HRID 500630 반응식
[OH-:1].[K+].[CH3:3][C:4]([N:23]1[CH2:28][CH2:27][CH:26]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:25][CH2:24]1)([CH3:22])[CH2:5][CH2:6][C:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:8]#[N:9]>CC(O)(CC)CC>[NH3:9].[CH3:22][C:4]([N:23]1[CH2:24][CH2:25][CH:26]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:27][CH2:28]1)([CH3:3])[CH2:5][CH2:6][C:7]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:8]([NH2:9])=[O:1]

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 594238715-Methyl-5-(4-phenoxypiperidin-1-yl)-2,2-diphenylhexanenitrile

생성물 2

HCID 222AmmoniaHCID 160652685-Methyl-5-(4-phenoxypiperidin-1-yl)-2,2-diphenylhexanamide

시약·촉매·용매 1

HCID 64933-methyl-3-Pentanol용매

실험 절차

Potassium hydroxide (512 mg, 9.12 mmol) was added to a solution of the product of example 86 (200 mg, 0.46 mmol) in 3-methyl-3-pentanol (4 mL) and the mixture was heated Under reflux for 20 hours. The reaction mixture was then cooled to room temperature, concentrated in vacuo and the residue was partitioned between ethyl acetate (20 mL) and water (20 mL). The organic layer was separated, dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 100:0 to 90:10:1, afforded the title compound as a colourless glass in 93% yield, 193 mg.

후처리

  1. temperaturethe mixture was heated
  2. temperatureUnder reflux for 20 hours
  3. concentrationconcentrated in vacuo
  4. customthe residue was partitioned between ethyl acetate (20 mL) and water (20 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by column chromatography on silica gel
  9. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-bb80213b63cb4de19b52546b154bccd9
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772223B2

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