Acetic Acid → Azetidin-1-yl(7-(piperazin-1-yl)benzofuran-2-yl)methanone

HRID 535662

Reaction equation

HRID 535662 reaction equation
[N:1]1([C:5]([C:7]2[O:8][C:9]3[C:15]([N:16]4[CH2:21][CH2:20][N:19](CC5C=CC=CC=5)[CH2:18][CH2:17]4)=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.N>>[N:1]1([C:5]([C:7]2[O:8][C:9]3[C:15]([N:16]4[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]4)=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 222AmmoniaHCID 59636710Azetidin-1-yl(7-(4-benzylpiperazin-1-yl)benzofuran-2-yl)methanone

Product 1

HCID 59636763Azetidin-1-yl(7-(piperazin-1-yl)benzofuran-2-yl)methanone

Procedure

The compound was prepared according to the procedure disclosed in Example 39d starting from azetidin-1-yl(7-(4-benzylpiperazin-1-yl)benzofuran-2-yl)methanone (0.52 g, 1.38 mmol) and acetic acid (0.63 mL, 11.1 mmol). A solution of ammonia (3 mL, 7N in MeOH) was added to the mixture after the reaction was complete. The solvent was removed by rotary evaporation. The crude product was purified by flash chromatography (SiO2; gradient 0-10% ammonia (7N in MeOH) in DCM). Yield: 0.36 g (91%).

Workup

  1. customThe compound was prepared
  2. customThe solvent was removed by rotary evaporation
  3. customThe crude product was purified by flash chromatography (SiO2; gradient 0-10% ammonia (7N in MeOH) in DCM)

Sources & evidence

ORD record
ord-bf5e8c97bd894bfe8f4be3c7d9d811ef
Source dataset
uspto-grants-2014_10
Patent number
US08859534B2

Linked notes

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