Acetic Acid → HCID 58557648, compound

HRID 1969522Notes

Reaction equation

HRID 1969522 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[NH2:17].CC(O)=O.[BH3-]C#N.[Na+]>ClCCCl>[CH2:2]([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([NH:17][NH:16][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 70091tert-Butyl carbazateHCID 30849241-Benzyl-3-piperidone hydrochloride hydrateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 58557648HCID 58557648, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 1-benzylpiperidin-3-one hydrochloride (1.00 g, 4.10 mmol), tert-butyl hydrazinecarboxylate (0.596 g, 4.51 mmol), and AcOH (0.470 mL, 8.21 mmol) in DCE (20 mL) was stirred at ambient temperature for about 1 h then NaCNBH3 (0.258 g, 4.10 mmol) was added. The reaction mixture was stirred at ambient temperature for about 16 h. The reaction mixture was quenched by the addition of saturated aqueous NaHCO3 (50 mL). The organic layer was separated, concd under reduced pressure and purified by RP-HPLC (Table 1, Method h) to afford tert-butyl 2-(1-benzylpiperidin-3-yl)hydrazinecarboxylate (1.25 g, 100%) as a clear oil: LC/MS (Table 1, Method b) Rt=1.66 min; MS m/z: 306 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for about 16 h
  2. customThe reaction mixture was quenched by the addition of saturated aqueous NaHCO3 (50 mL)
  3. customThe organic layer was separated
  4. custompurified by RP-HPLC (Table 1, Method h)

Sources & evidence

ORD record
ord-40724d74d3c44fee8d3f111b049aff41
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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