tert-Butyl 4-(3-fluoroanilino)piperidine-1-carboxylate → N-(3-fluorophenyl)piperidin-4-amine

HRID 906340ノート

反応式

HRID 906340 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1>Cl.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 1

HCID 23137591tert-Butyl 4-(3-fluoroanilino)piperidine-1-carboxylate

生成物 1

HCID 4778195N-(3-fluorophenyl)piperidin-4-amine収率 87.6%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 1,1-dimethylethyl 4-[(3-fluorophenyl)amino]-1-piperidinecarboxylate (D3) (2.30 g) in 2M HCl (5 ml) and 1,4-dioxane (40 ml) was heated at 70° C. with stirring overnight. On cooling, the solvent was removed in vacuo and the residue diluted with 2M NaOH solution and extracted with 9:1 EtOAc/tBuOH (×2). The organics were dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow solid (1.33 g). δH (CDCl3, 250 MHz) 7.07 (1H, q), 6.33 (3H, m), 3.83 (1H, br s), 3.33 (1H, br s), 3.12 (2H, m), 2.71 (2H, m), 2.04 (2H, m), 1.30 (2H, m).

後処理

  1. temperatureOn cooling
  2. customthe solvent was removed in vacuo
  3. additionthe residue diluted with 2M NaOH solution
  4. extractionextracted with 9:1 EtOAc/tBuOH (×2)
  5. dry with materialThe organics were dried (MgSO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e30d4b3f04b6472faf26622d055f4e34
出典データセット
uspto-grants-2011_09
特許番号
US08012981B2

反応ノート

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