Sulfuric Acid → 4-[(cyclohexylamino)methyl]-3,3-diphenyldihydro-2(3H)-furanone

HRID 2285768

Reaction equation

HRID 2285768 reaction equation
[CH:1]1([N:7]2[CH2:10][CH:9]([C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:12]#N)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)[OH:27].[OH-:31].[Na+]>>[CH:1]1([NH:7][CH2:8][CH:9]2[CH2:10][O:31][C:12](=[O:27])[C:11]2([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 12822284alpha-(1-Cyclohexyl-3-azetidinyl)-alpha,alpha-diphenylacetonitrile

Product 1

HCID 128222864-[(cyclohexylamino)methyl]-3,3-diphenyldihydro-2(3H)-furanoneYield 20%

Conditions

Temperature
120 °C

Procedure

To 41.0 g. (0.12 mole) of α-(1-cyclohexyl-3-azetidinyl)-α,α-diphenylacetonitrile was added 100 g. of a 70% solution of sulfuric acid, and the mixture was stirred and heated at 120° C. for 48 hrs. The solution was then poured over ice and made basic with 50% sodium hydroxide, and extracted with chloroform. The organic layer was dried, filtered, and concentrated in vacuo. The residue was crystallized twice from isopropyl ether, the crystallized material weighed 8.0 g. (20% yield) and melted at 129°-131° C.

Workup

  1. additionThe solution was then poured over ice
  2. extractionextracted with chloroform
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized twice from isopropyl ether

Sources & evidence

ORD record
ord-770240a822554d0cadfd74992670b5b7
Source dataset
uspto-grants-1982_04
Patent number
US04324791

Linked notes

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