Hydrazine hydrate (1:1) → HCID 178473788, compound

HRID 713417Notes

Reaction equation

HRID 713417 reaction equation
F[C:2]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:14])[CH3:13])[CH2:8][CH2:7]1)=O.O.[NH2:21][NH2:22]>CCCCO>[F:19][C:17]1[CH:18]=[C:2]2[C:3]([C:4]([CH:6]3[CH2:11][CH2:10][N:9]([C:12](=[O:14])[CH3:13])[CH2:8][CH2:7]3)=[N:21][NH:22]2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27407071-Acetyl-4-(2',4'-difluorobenzoyl)piperidine

Product 1

HCID 178473788HCID 178473788, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 1-[4-(2,4-difluoro-benzoyl)-piperidin-1-yl]-ethanone (1.7 g, 6.4 mmol), 6 mL of hydrazine hydrate and 13 mL of n-BuOH was refluxed for 48 hours. The reaction mixture was concentrated in vacuo, the residue was diluted with water (30 mL) and then extracted with ethyl acetate (50 mL). The solvent was removed in vacuo to yield the crude product as an oil. It was washed with heptane and the solvent was filtered to yield the title product (0.60 g, 2.3 mmol, 36% yield) as a white solid. MS (ESI) m/z 261.6 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.44 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with water (30 mL)
  3. extractionextracted with ethyl acetate (50 mL)
  4. customThe solvent was removed in vacuo
  5. customto yield the crude product as an oil
  6. washIt was washed with heptane
  7. filtrationthe solvent was filtered

Sources & evidence

ORD record
ord-193ad77b567d42e1a16a2465216cc9d1
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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