Water → 2,3,4,4a,9,9a-Hexahydro-1H-indeno(2,1-b)pyridine-6-carbonitrile

HRID 873036ノート

反応式

HRID 873036 の反応式
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]2[C:7]3[CH:8]=[C:9]([C:14]([NH2:16])=O)[CH:10]=[CH:11][C:12]=3[CH2:13][CH:2]12.O=P(Cl)(Cl)Cl.O>O1CCOCC1>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]2[C:7]3[CH:8]=[C:9]([C:14]#[N:16])[CH:10]=[CH:11][C:12]=3[CH2:13][CH:2]12

参加物

5

反応物 3

HCID 962Water2 回HCID 24813Phosphorus oxychlorideHCID 712643652,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-6-carboxamide

生成物 1

HCID 671950702,3,4,4a,9,9a-Hexahydro-1H-indeno(2,1-b)pyridine-6-carbonitrile

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
25 °C

実験手順

A mixture of 2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-6-carboxamide (I), hydrogen chloride salt (7.5 Kg, 25.2 mol) and dioxane (15 L) is stirred for 30 minutes at 25° C. and treated with POCl3 (7.77 Kg, 50.4 mol). The mixture is heated to 80° C. over 1 hour and held at 80° C. for 2 hours. The mixture is cooled to 20-25° C., treated over about 30 minutes with a solution of water (1.376 L, 75.6 mol) in dioxane (30 L), stirred for 30 minutes, and treated with additional water (1.376 L, 75.6 mol). The resulting slurry is stirred at 25° C. for about 18 hours and filtered. The resulting filter cake is washed portion-wise with 3.0 L of 1% H2O in 1,4-dioxane and dried for about 18 hours at ˜50° C. to provide 2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-6-carbonitrile (III) in the form of the hydrogen chloride salt. Yield: 4.73 Kg, 20.16 mol; 80%.

後処理

  1. temperatureThe mixture is heated to 80° C. over 1 hour
  2. waitheld at 80° C. for 2 hours
  3. temperatureThe mixture is cooled to 20-25° C.
  4. stirringstirred for 30 minutes
  5. stirringThe resulting slurry is stirred at 25° C. for about 18 hours
  6. filtrationfiltered
  7. filtrationThe resulting filter cake
  8. washis washed portion-wise with 3.0 L of 1% H2O in 1,4-dioxane
  9. customdried for about 18 hours at ˜50° C.

出典と根拠

ORDレコード
ord-1b41c2ba8bb84b9dbf2da3f7aaeef945
出典データセット
uspto-grants-2015_03
特許番号
US08975405B2

反応ノート

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