Tetrahydrofuran → HCID 57470084, compound

HRID 1260244Notes

Reaction equation

HRID 1260244 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:13][N:12]([C:14](=O)[CH2:15][CH3:16])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.O.O.Cl[Sn]Cl.[H-].[H-].[H-].[H-].[Li+].[Al+3].O1CCCC1>C(O)C>[CH2:14]([N:12]1[CH2:11][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)[CH2:13]1)[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 61436Stannous chloride dihydrateHCID 21226445Aluminium lithium hydrideHCID 574700801-(3-(4-Nitrophenyl)azetidin-1-yl)propan-1-one

Product 1

HCID 57470084HCID 57470084, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(3-(4-Nitrophenyl)azetidin-1-yl)propan-1-one (3.16 g, 13.49 mmol) was dissolved in ethanol (200 ml) and SnCl2.2H2O (15.20 g, 67.45 mmol) was added. The resulting mixture was refluxed for 8 h and then the solvent was removed under vacuum. The raw material was dissolved in ethyl acetate and washed successively with 2N aqueous NaOH (×2) and water. The organic layer was dried (Na2SO4), filtered through a pad of celite and evaporated. The crude 1-[3-(4-amino-phenyl)-azetidin-1-yl]-propan-1-one was then dissolved in tetrahydrofuran (THF) (200 ml) and 1M LiAlH4 in tetrahydrofuran (19.5 ml, 19.5 mmol) was added dropwise at 0° C. After stirring at room temperature for 2 h, the reaction mixture was carefully quenched with THF/H2O 9:1 (20 ml) at 0° C., then filtered through a pad of celite and the solvents were removed under reduced pressure. The crude 4-(1-propyl-azetidin-3-yl)-phenylamine was used without any further purification for the next step.

Workup

  1. temperatureThe resulting mixture was refluxed for 8 h
  2. customthe solvent was removed under vacuum
  3. dissolutionThe raw material was dissolved in ethyl acetate
  4. washwashed successively with 2N aqueous NaOH (×2) and water
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered through a pad of celite
  7. customevaporated
  8. dissolutionThe crude 1-[3-(4-amino-phenyl)-azetidin-1-yl]-propan-1-one was then dissolved in tetrahydrofuran (THF) (200 ml)
  9. customthe reaction mixture was carefully quenched with THF/H2O 9:1 (20 ml) at 0° C.
  10. filtrationfiltered through a pad of celite
  11. customthe solvents were removed under reduced pressure
  12. customThe crude 4-(1-propyl-azetidin-3-yl)-phenylamine was used without any further purification for the next step

Sources & evidence

ORD record
ord-48a3f46caa5b49b6a8d77e86c20d4b29
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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