Hydrazine → 3-(4-(4-Fluorophenyl)piperidin-1-yl)propan-1-amine

HRID 2085402Notes

Reaction equation

HRID 2085402 reaction equation
[NH2:1]N.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18]C3C=CC=C4C(NC(=O)C=34)=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1>CO>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][NH2:1])[CH2:14][CH2:15]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 227294733-[4-(4-Fluorophenyl)piperidin-1-yl]propylphthalimide

Product 1

HCID 101985993-(4-(4-Fluorophenyl)piperidin-1-yl)propan-1-amineYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrazine (4 mL) was added to a solution of 3-[4-(4-fluorophenyl)piperidin-1-yl]propylphthalimide (4.50 g, 12.3 mmol) in methanol (200 mL), and the mixture was stirred at reflux for 8 h. The solution was cooled to room temperature, and the resulting white solid which formed was filtered and washed with methanol (20 mL). The solvent was evaporated from the filtrate and residue was dried under vacuum for 4 h. The crude product was dissolved in 50 mL of chloroform, stirred for 1 h, and filtered. The white solid was washed with additional chloroform (20 mL), the solvent was evaporated from the combined filtrates to leave the crude product as an oil. The oil was purified by column chromatography (dichloromethane/methanol/2 M ammonia in methanol, 10/3/1), giving the desired product (2.70 g, 93%). 1H NMR δ 1.60-1.83 (m, 6H), 1.96-2.07 (m, 4H), 2.40-2.55 (m, 3H), 2.70-2.85 (br t, 2H), 3.03-3.07 (br d, 2H), 6.93-7.00 (m, 2H), 7.14-7.20 (m, 2H).

Workup

  1. temperatureat reflux for 8 h
  2. customthe resulting white solid which formed
  3. filtrationwas filtered
  4. washwashed with methanol (20 mL)
  5. customThe solvent was evaporated from the filtrate and residue
  6. customwas dried under vacuum for 4 h
  7. dissolutionThe crude product was dissolved in 50 mL of chloroform
  8. stirringstirred for 1 h
  9. filtrationfiltered
  10. washThe white solid was washed with additional chloroform (20 mL)
  11. customthe solvent was evaporated from the combined filtrates
  12. customto leave the crude product as an oil
  13. customThe oil was purified by column chromatography (dichloromethane/methanol/2 M ammonia in methanol, 10/3/1)

Sources & evidence

ORD record
ord-0a0138622fc347c395f35ef4cdcca8bd
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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