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

HRID 371933Notes

Reaction equation

HRID 371933 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 and dried over magnesium sulfate and evaporated to a pale amber liquid. This liquid is crystallized from hexane to give the product, 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
  7. customto give the product, mp 63°-65° C.

Sources & evidence

ORD record
ord-36f7f18d51914580b6c174cc800b5c12
Source dataset
uspto-grants-1978_05
Patent number
US04088652

Reaction notes

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