Sulfuric Acid → 6-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 717796ノート

反応式

HRID 717796 の反応式
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9]N.OS(O)(=O)=O.[CH3:16][N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1>O1CCOCC1>[Cl:2][C:3]1[C:4]2[NH:9][C:20]3[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][C:19]=3[C:5]=2[CH:6]=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 740491-Methyl-4-piperidoneHCID 4432872-Chlorophenylhydrazine hydrochloride

生成物 1

HCID 50915806-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole収率 30.9%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To a suspension of 2-chlorophenyl hydrazine hydrochloride (19.7 g, 0.110 mol) in dioxane (190 mL) at RT was added conc. H2SO4 (8 mL, 0.150 mol) dropwise and the reaction mixture was stirred for 10 min. To this was added N-methyl-4-piperidone (17.53 g, 0.154 mol) and the reaction mixture was stirred at RT for 20 min, then heated at 80° C. for 4 h. The reaction was monitored by TLC. The solvent was evaporated and pH adjusted to pH 8-9 with saturated sodium bicarbonate solution. The product was extracted with EtOAc (3×300 mL). The combined organic layer was washed with water and brine, dried over sodium sulfate, and concentrated under vacuum. The crude product was purified by recrystallization (Ether/Hexane). The filtered solid was dried in vacuo to obtain 7.5 g of product as a brown solid. 1H NMR (CDCl3, freebase) d (ppm): 8.10 (bs, 1H), 7.30 (d, 1H), 7.10 (d, 1H), 7.0 (t, 1H), 3.62 (s, 2H), 2.90 (m, 2H), 2.82 (m, 2H), 2.38 (s, 3H).

後処理

  1. stirringthe reaction mixture was stirred at RT for 20 min
  2. customThe solvent was evaporated
  3. extractionThe product was extracted with EtOAc (3×300 mL)
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by recrystallization (Ether/Hexane)
  8. customThe filtered solid was dried in vacuo

出典と根拠

ORDレコード
ord-24ea880e26d44712858cc15187d6e6f6
出典データセット
uspto-grants-2015_11
特許番号
US09193728B2

反応ノート

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