Acetic Anhydride → 3-Acetyl-1-phenyl-3-azabicyclo[3.1.0]hexane

HRID 224284Notes

Reaction equation

HRID 224284 reaction equation
[C:1]1([C:7]23[CH2:12][CH:11]2[CH2:10][NH:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1.CCOCC.C(Cl)Cl>[C:13]([N:9]1[CH2:10][CH:11]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([CH2:12]2)[CH2:8]1)(=[O:15])[CH3:14]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 101300941-Phenyl-3-azabicyclo[3.1.0]hexane

Product 1

HCID 128913713-Acetyl-1-phenyl-3-azabicyclo[3.1.0]hexane

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To 15.9 g of 1-phenyl-3-azabicyclo[3.1.0]hexane in 20 ml of pyridine is added 20 ml of acetic anhydride. The mixture is allowed to stand overnight at room temperature and then evaporated to give an oil. This oil is dissolved in a mixture of ether and methylene chloride, washed with dilute hydrochloric acid and then sodium bicarbonate and dried over magnesium sulfate and evaporated to a pale amber liquid. This liquid is crystallized from hexane ot give the product 3-acetyl-1-phenyl-3-azabicyclo[3.1.0]hexane mp 63°-65° C.

Workup

  1. customevaporated
  2. customto give an oil
  3. washwashed with dilute hydrochloric acid
  4. dry with materialsodium bicarbonate and dried over magnesium sulfate
  5. customevaporated to a pale amber liquid
  6. customThis liquid is crystallized from hexane

Sources & evidence

ORD record
ord-98ab3472691f4cc5b26850c5d8bb1095
Source dataset
uspto-grants-1980_11
Patent number
US04231935

Reaction notes

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