Pyridine → 3-Acetyl-1-phenyl-3-azabicyclo[3.1.0]hexane

HRID 1903256Notes

Reaction equation

HRID 1903256 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.N1C=CC=CC=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>CCOCC.C(Cl)Cl>[C:19]([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:21])[CH3:20]

Participants

6

Reactant 3

HCID 1049PyridineHCID 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 2

HCID 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, dried over magnesium sulfate and evaporated to a pale amber liquid. This liquid is crystallized from hexane to give the product 3-acetyl-1-phenyl-3-azabicyclo[3.1.0]hexane, m.p. 63°-65° C.

Workup

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

Sources & evidence

ORD record
ord-c2847aaab2384788bf25a96187c72b50
Source dataset
uspto-grants-1984_03
Patent number
US04435419

Reaction notes

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