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

HRID 518817ノート

反応式

HRID 518817 の反応式
C([O-])=O.[NH4+].[C:5]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([O:24][CH:25]([CH3:27])[CH3:26])[CH:16]=2)[CH2:11][CH2:10]1)(=[O:7])[CH3:6]>CO.[Pd]>[C:5]([O:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([O:24][CH:25]([CH3:27])[CH3:26])[CH:16]=2)[CH2:13][CH2:14]1)(=[O:7])[CH3:6]

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 866979841-[4-Nitro-3-(propan-2-yloxy)phenyl]piperidin-4-yl acetate

生成物 1

HCID 866979851-[4-Amino-3-(propan-2-yloxy)phenyl]piperidin-4-yl acetate収率 39.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

622 mg of ammonium formate and 525 mg of Pd/C (10%) are added to a solution of 530 mg of 1-[4-nitro-3-(propan-2-yloxy)phenyl]piperidin-4-yl acetate in 13 ml of methanol. The reaction medium is microwave-heated at 80° C. for 5 minutes. The mixture is filtered on Clarcel, and the Clarcel is rinsed with methanol. The filtrate is concentrated under reduced pressure. The residue is taken up with 20 ml of ethyl acetate, 2 ml of water and 8 ml of a saturated aqueous sodium chloride solution. The two phases are separated and the aqueous phase is washed with 3 times 10 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated. The residue is purified on silica, elution being carried out with dichloromethane/MeOH (95/5), so as to give 190 mg of 1-[4-amino-3-(propan-2-yloxy)phenyl]piperidin-4-yl acetate in the form of a brown oil.

後処理

  1. filtrationThe mixture is filtered on Clarcel
  2. washthe Clarcel is rinsed with methanol
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customThe two phases are separated
  5. washthe aqueous phase is washed with 3 times 10 ml of ethyl acetate
  6. dry with materialThe combined organic phases are dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified on silica, elution

出典と根拠

ORDレコード
ord-c47ce6e9d8224a469c4eaa4bc7b0984f
出典データセット
uspto-grants-2015_08
特許番号
US09115140B2

反応ノート

読み込み中…