Hydrazinecarboxaldehyde → 4-(1-Benzylpiperidin-4-yl)-1-formylsemicarbazide

HRID 2217862Notes

Reaction equation

HRID 2217862 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(Cl)(O[C:19](=[O:25])OC(Cl)(Cl)Cl)Cl.[CH:27]([NH:29][NH2:30])=[O:28]>ClCCl.C(N(CC)CC)C>[CH:27]([NH:29][NH:30][C:19]([NH:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1)=[O:25])=[O:28]

Participants

6

Reactant 3

HCID 12229HydrazinecarboxaldehydeHCID 94429TriphosgeneHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 688114854-(1-Benzylpiperidin-4-yl)-1-formylsemicarbazideYield 173.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

1-(Phenylmethyl)4-piperidinamine (3 g) in dichloromethane (10 mL) and triethylamine (4.5 mL) were added dropwise to a stirred solution of triphosgene (1.55 g) in dichloromethane (20 mL) at 0° C. under nitrogen. The reaction mixture was allowed to warm to room temperature and stirred for 30 minutes. The mixture was cooled to 0° C. and formyl hydrazine (1.4 g) and triethylamine (4.5 mL) were added. The reaction was stirred at room temperature for 1 hour and then evaporated to dryness. Purification (SiO2, methanol:dichloromethane:ammonium hydroxide solution 5:95:1 as eluant) gave the sub-title compound (2.5 g).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringThe reaction was stirred at room temperature for 1 hour
  3. customevaporated to dryness
  4. customPurification (SiO2, methanol:dichloromethane:ammonium hydroxide solution 5:95:1 as eluant)

Sources & evidence

ORD record
ord-bc8c2e0478c449149c77d59388cb69d1
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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