Potassium Iodide → 2,2-Diphenyl-4-piperidin-1-ylbutanenitrile

HRID 2083671

반응식

HRID 2083671 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[I-].[K+].C(=O)(O)[O-].[K+].[C:14]1([C:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH2:23][CH2:24]Br)[C:21]#[N:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[C:26]1([C:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([CH2:23][CH2:24][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:21]#[N:22])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 8082PiperidineHCID 965754-Bromo-2,2-diphenylbutyronitrileHCID 516893Potassium Bicarbonate

생성물 1

HCID 2245772,2-Diphenyl-4-piperidin-1-ylbutanenitrile수율 66.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

1.96 Parts piperidine, 1.91 parts potassium iodide and 25 parts deionized water are combined and gently heated under a nitrogen atmosphere. To this slurry is then added 2.75 parts of potassium bicarbonate, followed by 7.51 parts of 2,2-diphenyl-4-bromobutyronitrile. The mixture is heated to reflux and maintained thereat for 4.5 hours. After cooling to room temperature, the reaction mixture is extracted three times with 14 part portions of ethyl ether. The ether extracts are combined, and extracted six times with 25 parts by volume portions of dilute acetic acid solution. The acid extracts are combined, basified to about pH 10 - 12 with 50% sodium hydroxide solution, and again extracted with ethyl ether. The ether extracts are combined, washed with water and saturated sodium chloride solution, and dried over anhydrous potassium carbonate. Removal of the solvent affords 2,2-diphenyl-4-piperidinobutyronitrile, identical to the product of Example 22, in a 66.6% yield.

후처리

  1. temperaturegently heated under a nitrogen atmosphere
  2. temperatureThe mixture is heated
  3. temperatureto reflux
  4. temperaturemaintained
  5. extractionthe reaction mixture is extracted three times with 14 part portions of ethyl ether
  6. extractionextracted six times with 25 parts by volume portions of dilute acetic acid solution
  7. extractionagain extracted with ethyl ether
  8. washwashed with water and saturated sodium chloride solution
  9. dry with materialdried over anhydrous potassium carbonate
  10. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-ac663a5a1f92405a993d0944f95d3bf9
출처 데이터셋
uspto-grants-1978_04
특허 번호
US04086234

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