Sulfuric Acid → HCID 21486051, compound

HRID 1414919Notes

Reaction equation

HRID 1414919 reaction equation
[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([CH:10]2[CH2:14][CH2:13][N:12]([CH:15]([CH3:17])[CH3:16])[CH2:11]2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)[OH:25].[OH-].[Na+]>>[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([CH:10]2[CH2:14][CH2:13][N:12]([CH:15]([CH3:17])[CH3:16])[CH2:11]2)[C:8]([NH2:9])=[O:25])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 21486052HCID 21486052, compound

Product 1

HCID 21486051HCID 21486051, compound

Procedure

A solution of 29.0 g. of α,α-diphenyl-α-(1-isopropyl-3-pyrrolidinyl)acetonitrile in 100 ml. of conc. sulfuric acid was heated at 80° C. for 18 hours. The reaction mixture was poured onto ice, the resulting cold acidic solution made basic using sodium hydroxide and the basic solution extracted with chloroform. The dried chloroform extract was concentrated and the residue crystallized from isooctane. The solid was recrystallized from isopropyl ether to give 13.2 g. (43%) of product which melted at 110.5°-112.5° C.

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionthe basic solution extracted with chloroform
  3. extractionThe dried chloroform extract
  4. concentrationwas concentrated
  5. customthe residue crystallized from isooctane
  6. customThe solid was recrystallized from isopropyl ether
  7. customto give 13.2 g

Sources & evidence

ORD record
ord-dc4009d637eb46fbbc9dc7993053d876
Source dataset
uspto-grants-1977_01
Patent number
US04002766

Reaction notes

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