Pyrrolidine → HCID 21484878, compound

HRID 1973072Notes

Reaction equation

HRID 1973072 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([CH2:10][CH:11](Br)[CH3:12])[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1CCCC1>>[C:14]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(/[CH:10]=[CH:11]/[CH3:12])[C:8]#[N:9])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 21484879HCID 21484879, compound

Product 1

HCID 21484878HCID 21484878, compound

Procedure

A solution of 10.0 parts of 2,2-diphenyl-4-bromopentanenitrile in 47 parts pyrrolidine is heated to reflux for 17 hours under a nitrogen atmosphere. Then, the solution is cooled, and stripped in vacuo to leave a brown oil which is partitioned between ethyl ether and dilute hydrochloric acid. The ether phase is separated, washed with dilute sodium bicarbonate, dried over anhydrous sodium sulfate, and stripped in vacuo. The residual liquid is then distilled to afford, as a colorless liquid, 2,2-diphenyl-3-trans-pentenenitrile, boiling at about 115°-123° C. at 0.1 mm pressure. This compound is represented by the following structural formula. ##STR6##

Workup

  1. temperatureto reflux for 17 hours under a nitrogen atmosphere
  2. temperatureThen, the solution is cooled
  3. customto leave a brown oil which
  4. customis partitioned between ethyl ether and dilute hydrochloric acid
  5. customThe ether phase is separated
  6. washwashed with dilute sodium bicarbonate
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe residual liquid is then distilled

Sources & evidence

ORD record
ord-6d7319a4b0e74f3397137edab1512475
Source dataset
uspto-grants-1976_12
Patent number
US03996214

Reaction notes

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