Ammonium formate → 2-{4-[4-Amino-3-(propan-2-yloxy)phenyl]piperidin-1-yl}ethanol

HRID 518868ノート

反応式

HRID 518868 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][OH:18])[CH2:14][CH:15]=2)=[CH:6][C:5]=1[O:19][CH:20]([CH3:22])[CH3:21])([O-])=O.C([O-])=O.[NH4+]>C(O)C.ClCCl.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][OH:18])[CH2:14][CH2:15]2)=[CH:6][C:5]=1[O:19][CH:20]([CH3:22])[CH3:21]

参加物

6

反応物 2

HCID 2723923Ammonium formateHCID 866980212-{4-[4-nitro-3-(propan-2-yloxy)phenyl]-3,6-dihydropyridin-1(2H)-yl}ethanol

生成物 1

HCID 683600452-{4-[4-Amino-3-(propan-2-yloxy)phenyl]piperidin-1-yl}ethanol収率 90.8%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

A mixture of 150 mg of 10% palladium-on-carbon and 400 mg of 2-{4-[4-nitro-3-(propan-2-yloxy)phenyl]-3,6-dihydropyridin-1(2H)-yl}ethanol in 15 ml of ethanol is heated at 80° C. with stirring. 1.25 g of ammonium formate are then added in two portions. After stirring at 80° C. for 1 h, the mixture is allowed to return to ambient temperature and is filtered on Clarcel. The Clarcel is rinsed with 200 ml of ethanol and the filtrate is concentrated under vacuum, so as to obtain a residue which is solubilised in 150 ml of dichloromethane. The organic phase is washed three times with 70 ml of a saturated potassium carbonate solution, and the aqueous phase is extracted twice with 100 ml of dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and concentrated under vacuum, so as to obtain 330 mg of 2-{4-[4-amino-3-(propan-2-yloxy)phenyl]piperidin-1-yl}ethanol used without further purification.

後処理

  1. stirringAfter stirring at 80° C. for 1 h
  2. customto return to ambient temperature
  3. filtrationis filtered on Clarcel
  4. washThe Clarcel is rinsed with 200 ml of ethanol
  5. concentrationthe filtrate is concentrated under vacuum
  6. customso as to obtain a residue which
  7. washThe organic phase is washed three times with 70 ml of a saturated potassium carbonate solution
  8. extractionthe aqueous phase is extracted twice with 100 ml of dichloromethane
  9. dry with materialThe combined organic phases are dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-3c31278b78b54634b06ecf573cacb6a8
出典データセット
uspto-grants-2015_08
特許番号
US09115140B2

反応ノート

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