Potassium Hydroxide → Ammonia

HRID 500630ノート

反応式

HRID 500630 の反応式
[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]

参加物

5

反応物 2

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 64933-methyl-3-Pentanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bb80213b63cb4de19b52546b154bccd9
出典データセット
uspto-grants-2010_08
特許番号
US07772223B2

反応ノート

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