Acetic Acid → 3-Methyl-N-propyl-1H-indol-1-amine

HRID 2217088ノート

反応式

HRID 2217088 の反応式
[BH4-].[Na+].[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([N:13]=[CH:14][CH2:15][CH3:16])[CH:5]=1.C(O)(=O)C.[H][H]>CN1C(=O)CCC1.O.C(O)C>[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([NH:13][CH2:14][CH2:15][CH3:16])[CH:5]=1

参加物

8

反応物 4

HCID 176Acetic Acid2 回HCID 4311764Sodium borohydride2 回HCID 688630783-Methyl-N-propylidene-1H-indol-1-amineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 219460633-Methyl-N-propyl-1H-indol-1-amine収率 96%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒4 回HCID 13387N-methyl-2-pyrrolidone溶媒2 回

反応条件

温度
30 °C

実験手順

In a 800 L vessel, prepare a solution of 3.0 kg (74.4 mol) sodium borohydride and 26.8 kg (124 mol, 86% purity) 3-methyl-N-(propylidene)-1H-indol-1-amine in 108 kg NMP. Prepare a solution of 4.5 kg (74.4 mol) glacial acetic acid in 27 kg NMP. Add the acetic acid solution over a period of about 30 nm at 30° C. to the sodium borohydride solution. Immediately hydrogen is evolved. Stir the reaction mixture at 30° C. until completion of the reaction (˜1 h). Add 6.3 kg ethanol to the reaction mixture, foaming occurs immediately. The reaction mixture is then worked-up by adding additional 80 L water cautiously. Attention is taken during the addition of water such that foaming is controlled, slow addition of water is recommended especially in the beginning to avoid uncontrolled foaming. Care is taken to ensure no or only minimal foaming occurs while the first 1–2 L of water is added. The reaction mixture is allowed to stand over night. Extract the water phase three times with 45 kg n-heptane and wash the combined organic phases with 66 L water. Evaporate the combined organic phases to dryness. This results in 22.4 kg 3-methyl-N-propyl-1H-indol-1-amine (yield 90%, 94% purity) as a brown liquid.

後処理

  1. customuntil completion of the reaction (˜1 h)
  2. additionis added
  3. waitto stand over night
  4. extractionExtract the water phase three times with 45 kg n-heptane
  5. washwash the combined organic phases with 66 L water
  6. customEvaporate the combined organic phases to dryness

出典と根拠

ORDレコード
ord-cfa297d152bc4aef9f8cb3d3b4cedcd4
出典データセット
uspto-grants-2006_09
特許番号
US07112682B2

反応ノート

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