Sulfuric Acid → alpha,alpha-Diphenyl-1-phenylmethyl-3-pyrrolidineacetamide

HRID 1981909Notes

Reaction equation

HRID 1981909 reaction equation
S(=O)(=O)(O)O.[CH2:6]([N:13]1[CH2:17][CH2:16][CH:15]([C:18]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:19]#[N:20])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-:33].[Na+]>C(Cl)(Cl)Cl>[C:21]1([C:18]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([CH:15]2[CH2:16][CH2:17][N:13]([CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:14]2)[C:19]([NH2:20])=[O:33])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 13633740alpha-(1-Benzyl-3-pyrrolidinyl)-alpha,alpha-diphenylacetonitrile

Product 1

HCID 13633759alpha,alpha-Diphenyl-1-phenylmethyl-3-pyrrolidineacetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 250 ml of concentrated sulfuric acid under agitation was added, slowly at 70° C., 170 g (0.48 mole) of α-(1-benzyl-3-pyrrolidinyl)-α,α-diphenylacetonitrile. Stirring was continued for 16 hr at 75°-80° C. The solution was cooled and poured into a mixture of ice, 50% sodium hydroxide solution and chloroform. The chloroform layer was separated and the aqueous phase extracted three more times with chloroform. The combined chloroform layers were dried and concentrated in vacuo to give 188 g of residual oil. A portion of the oil was crystallized in isopropanol and the solid recrystallized from a mix of isopropanol and isopropyl ether to give a light brown solid, m.p. 135°-138° C.

Workup

  1. temperatureThe solution was cooled
  2. customThe chloroform layer was separated
  3. extractionthe aqueous phase extracted three more times with chloroform
  4. dry with materialThe combined chloroform layers were dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8e1de76195b49bb980043b64622b2db
Source dataset
uspto-grants-1986_06
Patent number
US04594343

Reaction notes

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