Water → 2,2-Diphenyl-4-(1,4-diazabicyclo[4.3.0]non-4-yl)butyronitrile

HRID 2083665Notes

Reaction equation

HRID 2083665 reaction equation
[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:10][CH2:11]Br)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:19]12[CH2:27][CH2:26][CH2:25][CH:24]1[CH2:23][NH:22][CH2:21][CH2:20]2.O.[OH-].[K+]>C(OCC)C>[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:10][CH2:11][N:22]2[CH2:23][CH:24]3[N:19]([CH2:27][CH2:26][CH2:25]3)[CH2:20][CH2:21]2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 965754-Bromo-2,2-diphenylbutyronitrileHCID 558578Octahydropyrrolo(1,2-a)pyrazine

Product 1

HCID 203569672,2-Diphenyl-4-(1,4-diazabicyclo[4.3.0]non-4-yl)butyronitrileYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
30 °C

Procedure

To 70.6 parts of 2,2-diphenyl-4-bromobutyronitrile is added 27 parts of 1,4-diazabicyclo[4.3.0]nonane, 63 parts of demineralized water and 15.5 parts of potassium hydroxide. The mixture is stirred and heated to 75° - 80° C. and then further heated to reflux. After 3.5 hours at reflux, the mixture is cooled to about 30° C. and 180 parts of ethyl ether is added. The aqueous layer is separated and discarded. The remaining ether layer is extracted three times with 100 parts by volume portions of 1% acetic acid in water, twice with 30% solutions of hydrochloric acid in water, and twice with 50% solutions of hydrochloric acid in water. The hydrochloric acid solution extracts are combined and basified to pH 11.0 with a 50% solution of potassium hydroxide in water. The resulting oil is extracted with three 150 part portions of chloroform. The chloroform extracts are combined, washed with 100 parts of a saturated sodium chloride solution, dried over anhydrous potassium carbonate, and stripped of solvent under reduced pressure. The resulting product, 2,2-diphenyl-4-(1,4-diazabicyclo[4.3.0]non-4-yl)butyronitrile, identical to the product of Example 7, is obtained in 86% yield. Correction of this yield to reflect the purity of the 1,4-diazabicyclo[4.3.0]-nonane (86.4%) results in a yield of 99.5% for this reaction.

Workup

  1. temperatureheated to 75° - 80° C.
  2. temperaturefurther heated to reflux
  3. temperatureAfter 3.5 hours at reflux
  4. customThe aqueous layer is separated
  5. extractionThe remaining ether layer is extracted three times with 100 parts by volume portions of 1% acetic acid in water
  6. extractionThe resulting oil is extracted with three 150 part portions of chloroform
  7. washwashed with 100 parts of a saturated sodium chloride solution
  8. dry with materialdried over anhydrous potassium carbonate

Sources & evidence

ORD record
ord-99234988a0174780aab8dc980d5ebf89
Source dataset
uspto-grants-1978_04
Patent number
US04086234

Reaction notes

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