Reaction #1174

Reaction equation

K2CO3

1-Benzyloxycarbonyl-4-phthalimidylpiperidine

hydrazine monohydrate

→

4-amino-1-benzyloxycarbonylpiperidine

Yield 85.0%

Solvents

ethanol

Brine

Conditions

Workup

1. 1
   Extractionthe mixture was extracted with 5% MeOH/CHCl3 (3×)
2. 2
   WashThe combined extracts were washed with 2N aq. HCl, 2N aq. NaOH, brine solution
3. 3
   Dryingdried over Na2SO4
4. 4
   Concentrationconcentrated

Procedure

1-Benzyloxycarbonyl-4-phthalimidylpiperidine (1.50 g, 4.27 mmol), prepared in Example 16B, was taken up in 20 mL of ethanol. To this solution was added hydrazine monohydrate (35 mL, 700 mmol) and this mixture was heated at 100° C. for 3 h. Brine solution (40 mL) and 10% aq. K2CO3 (60 mL) were added and the mixture was extracted with 5% MeOH/CHCl3 (3×). The combined extracts were washed with 2N aq. HCl, 2N aq. NaOH, brine solution, dried over Na2SO4 and concentrated to give 0.847 g, (85%) of 4-amino-1-benzyloxycarbonylpiperidine. [1H]-NMR(CDCl3) consistent with structure.

Source