Potassium Carbonate → 1-[(3-Bromophenyl)methyl]-4,4-difluoropiperidine

HRID 75584Notes

Reaction equation

HRID 75584 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.Cl.[F:11][C:12]1([F:18])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][N:15]1[CH2:16][CH2:17][C:12]([F:18])([F:11])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699793-Bromobenzyl bromideHCID 27583514,4-Difluoropiperidine hydrochloride

Product 1

HCID 866866881-[(3-Bromophenyl)methyl]-4,4-difluoropiperidineYield 99.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-bromobenzyl bromide (3.43 g, 13.73 mmol), 4,4-difluoro-piperidine hydrochloride (2.20 g, 13.97 mmol), and potassium carbonate (4.82 g, 34.86 mmol) in acetonitrile (50 mL) was stirred at RT for 16 h. The mixture was filtered and evaporated, and the residue partitioned between water (30 mL) and EtOAc (3×30 mL). The combined organic extracts were washed with water (2×50 mL) and dried (Na2SO4). The solvent was evaporated to give the title compound as a colourless oil (3.96 g, 99%). LCMS (Method 1): Rt 1.89 min, m/z 290/292 [MH+].

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customthe residue partitioned between water (30 mL) and EtOAc (3×30 mL)
  4. washThe combined organic extracts were washed with water (2×50 mL)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-76d9d70b99ad49e5b9edb7e01fad01cf
Source dataset
uspto-grants-2014_09
Patent number
US08835431B2

Reaction notes

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