Potassium Carbonate → 4-Amino-1-N-Cbz-piperidine

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Hydrazine hydrate (1:1)	HCID 24654	—
Reactant	Phenylmethyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-piperidinecarboxylate	HCID 21831105	—
Solvent	Ethanol	HCID 702	—
Solvent	Sodium chloride; water	HCID 57417360	—
Product	4-Amino-1-N-Cbz-piperidine	HCID 17846640	85%

Reaction Conditions

Temperature	100 °C

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05723490
Source dataset	uspto-grants-1998_03
ORD ID	ord-2cac9a20d7c04458add12877e56c0bdb
Source note	uspto-grants-1998_03