Hydrochloric Acid → HCID 70580866, compound

HRID 2163347Notes

Reaction equation

HRID 2163347 reaction equation
S(=O)(=O)(O)[OH:2].[C:6]1([C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH:15]2[CH2:18][N:17]([CH3:19])[CH2:16]2)[C:13]#[N:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[ClH:26]>CC(CC(C)C)=O>[ClH:26].[C:6]1([C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH:15]2[CH2:18][N:17]([CH3:19])[CH2:16]2)[C:13]([NH2:14])=[O:2])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 12822283HCID 12822283, compound

Product 1

HCID 70580866HCID 70580866, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
70 °C

Procedure

To 60 ml. of concentrated sulfuric acid preheated to 60° C. was added 21.7 g. (0.082 mole) of α,α-diphenyl-α-(1-methyl-3-azetidinyl)acetonitrile at a rate so as to maintain a temperature of 60°-70° C. The solution obtained was heated to 70° C. for 18 hrs. and extracted with chloroform. The chloroform extract was dried over sodium sulfate and concentrated and the residue crystallized from ethyl acetate-isopropyl alcohol to give 13.8 g. of the free base (60%) melting at 171°-174° C. The base was treated with hydrogen chloride in isobutyl methyl ketone and the salt recrystallized from isopropyl alcohol to give 9 g. of product melting at 182°-185° C.

Workup

  1. custompreheated to 60° C.
  2. additionwas added 21.7 g
  3. customThe solution obtained
  4. extractionand extracted with chloroform
  5. extractionThe chloroform extract
  6. dry with materialwas dried over sodium sulfate
  7. concentrationconcentrated
  8. customthe residue crystallized from ethyl acetate-isopropyl alcohol
  9. customto give 13.8 g
  10. customthe salt recrystallized from isopropyl alcohol
  11. customto give 9 g

Sources & evidence

ORD record
ord-3252311f5938470eb439cc840957c703
Source dataset
uspto-grants-1979_01
Patent number
US04133881

Reaction notes

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