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

HRID 873036노트

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HRID 873036 반응식
[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

참가 물질

5

반응물 3

HCID 962Water2회HCID 24813Phosphorus oxychlorideHCID 712643652,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-6-carboxamide

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

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온도
25 °C

실험 절차

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%.

후처리

  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.

출처 및 근거

ORD 기록
ord-1b41c2ba8bb84b9dbf2da3f7aaeef945
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975405B2

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