Tetrahydrofuran → 4-[(1-Methyl-3-piperidinyl)oxy]benzenamine

HRID 1830032ノート

反応式

HRID 1830032 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1COCC1.[CH3:16][N:17]1[CH2:22][CH2:21][CH2:20][CH:19]([OH:23])[CH2:18]1.F[C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=1>CCO.[Pd].O>[CH3:16][N:17]1[CH2:22][CH2:21][CH2:20][CH:19]([O:23][C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[CH2:18]1

参加物

8

反応物 4

HCID 8028TetrahydrofuranHCID 9590p-FluoronitrobenzeneHCID 980163-Piperidinol, 1-methyl-HCID 3251421Potassium bis(trimethylsilyl)amide

生成物 1

HCID 220554854-[(1-Methyl-3-piperidinyl)oxy]benzenamine

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

KHMDS (1.1 equivalent) was added to a THF solution of 1-methylpiperidin-3-ol (1 equivalent) at 0° C. and stirred until H2 evolution ceased. 1-fluoro-4-nitrobenzene (1 equivalent) was then added and the solution was allowed to warm to room temperature. After 2 hours, water was added and the mixture was extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, and concentrated in vacuo to give a bright yellow oil which was directly used in the reduction step. The oil (1 equivalent) and a catalytic amount of 10% Pd/C were suspended in anhydrous EtOH at room temperature. The reaction flask was evacuated and subsequently filled with H2. After stirring for 18 hours, the mixture was filtered through Celite, and the solvent was concentrated in vacuo to yield 4-(1-methyl-3-piperidyloxy)phenylamine. LC/MS (m/z) 207.2 (MH+), Rt 0.47 minutes.

後処理

  1. extractionthe mixture was extracted with EtOAc (3×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give a bright yellow oil which
  5. customThe reaction flask was evacuated
  6. additionsubsequently filled with H2
  7. stirringAfter stirring for 18 hours
  8. filtrationthe mixture was filtered through Celite
  9. concentrationthe solvent was concentrated in vacuo

出典と根拠

ORDレコード
ord-70510dc3afdc4dafb01e3b3233af75df
出典データセット
uspto-grants-2006_06
特許番号
US07064215B2

反応ノート

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