Dimethylformamide → HCID 22707847, compound

HRID 353327Notes

Reaction equation

HRID 353327 reaction equation
[H-].[Na+].C([N:10]1[CH2:15][CH2:14][CH:13](O)[CH2:12][CH2:11]1)(OC(C)(C)C)=O.[F:17][C:18]1[CH:25]=[CH:24][C:21](CBr)=[CH:20][CH:19]=1.CN(C)[CH:28]=[O:29]>>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH:13]2[CH2:12][CH2:11][N:10]([O:29][CH3:28])[CH2:15][CH2:14]2)=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 22707847HCID 22707847, compound

Procedure

Ninety-five percent dry sodium hydride is weighted in a 25 mL vial. Boc-(4-hydroxy)-piperidine (1 g, 4.97 mmol) in 10 mL of dimethyl formamide is added and the reaction mixture is stirred at room temperature for 15 minutes 4-fluoro benzyl bromide (1.4 g, 7.5 mmol) is added and the reaction mixture is stirred at room temperature for 16 hours, then quenched with water and diluted with ethyl acetate. The organic layer was washed with brine, then dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane 1:10. The Boc-protected amine is dissolved in 3 mL of dichloromethane and 3 mL of trifluoroacetic acid and the reaction mixture is stirred at room temperature for 16 hours and the solvent is evaporated to give 1.8 g of 4-(4-fluorophenyl)-methoxy piperidine. MS: M+H=210.1319.

Workup

  1. additionis added
  2. customquenched with water
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane 1:10
  8. dissolutionThe Boc-protected amine is dissolved in 3 mL of dichloromethane
  9. stirring3 mL of trifluoroacetic acid and the reaction mixture is stirred at room temperature for 16 hours
  10. customthe solvent is evaporated

Sources & evidence

ORD record
ord-e72c30200df948e1a087ce65609a7ece
Source dataset
uspto-grants-2004_06
Patent number
US06750228B1

Reaction notes

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