Piperidine-4-carboxylic acid [3-(4-fluoro-phenoxy)-phenyl]-amide hydrochloride → HCID 69223903, compound

HRID 29887

Reaction equation

HRID 29887 reaction equation
Cl.[F:2][C:3]1[CH:24]=[CH:23][C:6]([O:7][C:8]2[CH:9]=[C:10]([NH:14][C:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=O)[CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1>C1COCC1>[F:2][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[CH:9]=[C:10]([NH:14][CH2:15][CH:17]3[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)[CH:11]=[CH:12][CH:13]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 1

HCID 86607288Piperidine-4-carboxylic acid [3-(4-fluoro-phenoxy)-phenyl]-amide hydrochloride

Product 1

HCID 69223903HCID 69223903, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

A heavy-walled glass tube was charged with piperidine-4-carboxylic acid [3-(4-fluoro-phenoxy)-phenyl]-amide hydrochloride (Example 1D, 5.1 g, 0.016 mol) in dry THF (20 mL) followed by addition of BH3 (1 M in THF, 48 mL) at room temperature. The tube was sealed and then heated at 65° C. for 20 hours. The resulting reaction mixture was cooled to room temperature, evaporated to dryness, and quenched by the addition of 1 N HCl (5 mL) with stirring for 2 hours. The pH was then adjusted to pH 8 with 1 N ammonium hydroxide and the product was extracted with ethyl acetate (100 mL×2), dried over MgSO4, and concentrated to give an off-white solid (4.5 g, 93%).

Workup

  1. customThe tube was sealed
  2. customThe resulting reaction mixture
  3. temperaturewas cooled to room temperature
  4. customevaporated to dryness
  5. customquenched by the addition of 1 N HCl (5 mL)
  6. extractionthe product was extracted with ethyl acetate (100 mL×2)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-84426f913a7d4f5082159eb6e5063320
Source dataset
uspto-grants-2008_09
Patent number
US07423043B2

Linked notes

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