Pyridine → 3-(Cyanodiphenylmethyl)-1-pyrrolidinecarboxylic acid phenyl ester

HRID 1981907Notes

Reaction equation

HRID 1981907 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]#[N:15])[CH2:9]1)C1C=CC=CC=1.N1C=CC=CC=1.Cl[C:35]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:36]>C(Cl)Cl>[C:14]([C:13]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH:10]1[CH2:11][CH2:12][N:8]([C:35]([O:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:36])[CH2:9]1)#[N:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 13633740alpha-(1-Benzyl-3-pyrrolidinyl)-alpha,alpha-diphenylacetonitrile

Product 1

HCID 136337783-(Cyanodiphenylmethyl)-1-pyrrolidinecarboxylic acid phenyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 47 g (0.13 mole) of α-(1-benzyl-3-pyrrolidinyl)-α,α-diphenylacetonitrile and 10.58 g (0.13 mole) of pyridine in 400 ml of methylene chloride was added, dropwise at 0° C., 62.7 g (0.39 mole) of phenyl chloroformate. The reaction mixture was refluxed for 16 hr. The mixture was cooled and washed 3 times with water and twice with dilute sodium hydroxide solution. The methylene chloride layer was then dried, filtered and concentrated in vacuo. The resulting solid was recrystallized twice from ethyl acetate to give 23 g (50%) of title compound, m.p. 154°-155° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hr
  2. temperatureThe mixture was cooled
  3. washwashed 3 times with water
  4. dry with materialThe methylene chloride layer was then dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-94d979763816466d8789009279c09cc0
Source dataset
uspto-grants-1986_06
Patent number
US04594343

Reaction notes

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