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

HRID 1193983Notes

Reaction equation

HRID 1193983 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 ester

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 given 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-6ea4eed5e6124925a0bbd41b71c2c962
Source dataset
uspto-grants-1989_03
Patent number
US04812451

Reaction notes

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