Acetic Anhydride → Isopropyl Acetate

HRID 1155095Notes

Reaction equation

HRID 1155095 reaction equation
[N:1]12[CH2:13][CH:5]([CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=31)[NH:4][CH2:3][CH2:2]2.[C:14]([O:17][C:18](=[O:20])[CH3:19])(=[O:16])[CH3:15]>C1C=CC=CC=1>[C:14]([O:17][CH:12]([CH3:11])[CH3:7])(=[O:16])[CH3:15].[C:18]([N:4]1[CH:5]2[CH2:13][N:1]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[CH2:6]2)[CH2:2][CH2:3]1)(=[O:20])[CH3:19]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 12764421HCID 12764421, compound

Product 2

HCID 7915Isopropyl AcetateHCID 12764428HCID 12764428, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (10.5 g.) (the starting material of part A of Example 1), acetic anhydride (25 ml.) and benzene (50 ml.) was heated under reflux for four hours, then concentrated. Methanol was added to the residue, and the mixture was boiled and concentrated. Excess saturated potassium carbonate solution was added to an aqueous solution of the residue, and the mixture was extracted with chloroform. The chloroform extract was dried, filtered and concentrated. Recrystallization of the residue first from ether, then from ether-acetone, then from isopropyl acetate afforded 4-acetyl-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (2.25 g., m.r. 105°-106° C.), the compound of Formula VIII.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for four hours
  3. concentrationconcentrated
  4. additionMethanol was added to the residue
  5. concentrationconcentrated
  6. additionExcess saturated potassium carbonate solution was added to an aqueous solution of the residue
  7. extractionthe mixture was extracted with chloroform
  8. extractionThe chloroform extract
  9. customwas dried
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customRecrystallization of the residue first from ether

Sources & evidence

ORD record
ord-c81d5d581705422db9e194234c281db9
Source dataset
uspto-grants-1981_11
Patent number
US04299830

Reaction notes

Loading…