Hydrochloric Acid → HCID 66783848, compound

HRID 1182721Notes

Reaction equation

HRID 1182721 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([O:14][C:15](=O)[C:4]=2[CH:3]=1)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]3.B.Cl.[OH-].[Na+]>O1CCCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([O:14][CH2:15][C:4]=2[CH:3]=1)[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 14798Sodium HydroxideHCID 226607315-Fluoro-3h-spiro[isobenzofuran-1,4'-piperidin]-3-one

Product 1

HCID 66783848HCID 66783848, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 5-fluoro-3H-spiro[2-benzofuran-1,4′-piperidin]-3-one (420 mg, 1.9 mmol) in tetrahydrofuran (4.2 ml) was added dropwise a 1M borane solution in tetrahydrofuran (3.8 ml, 3.8 mmol) at 0° C. The mixture was refluxed overnight and then cooled to 0° C. HCl 5 N (2 ml) was added dropwise. The mixture was refluxed for 5 hours, cooled to 0° C., diluted with water and basified with NaOH 5 N (pH 10). The mixture was extracted 3 times with ethyl acetate. The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was stirred with ether and filtrated. The filtrate was concentrated in vacuo to provide 0.22 g (55%) of 5-fluoro-3H-spiro[2-benzofuran-1,4′-piperidine] as a light yellow oil.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperatureThe mixture was refluxed for 5 hours
  3. temperaturecooled to 0° C.
  4. extractionThe mixture was extracted 3 times with ethyl acetate
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. filtrationfiltrated
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e873bf3c1ab04fd1b19d87663f1703ad
Source dataset
uspto-grants-2014_03
Patent number
US08664216B2

Reaction notes

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