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

HRID 1078

Reaction equation

HRID 1078 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2C(=O)C3=CC=CC=C3C2=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.C([O-])([O-])=O.[K+].[K+]>C(O)C.[Cl-].[Na+].O>[NH2:17][CH:14]1[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 21831105Phenylmethyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-piperidinecarboxylate

Product 1

HCID 178466404-Amino-1-N-Cbz-piperidineYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

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.

Workup

  1. extractionthe mixture was extracted with 5% MeOH/CHCl3 (3×)
  2. washThe combined extracts were washed with 2N aq. HCl, 2N aq. NaOH, brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2cac9a20d7c04458add12877e56c0bdb
Source dataset
uspto-grants-1998_03
Patent number
US05723490

Linked notes

Loading…