Hydrochloric Acid → 4-Amino-1-(1-benzyloxycarbonyl-4-piperidinylmethyl)piperidine

HRID 1597308Notes

Reaction equation

HRID 1597308 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([NH:24]C(OC(C)(C)C)=O)[CH2:20][CH2:19]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)C>[NH2:24][CH:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH:14]2[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:12][CH2:13]2)[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 129861531-(1-Benzyloxycarbonyl-4-piperidinylmethyl)-4-(t-butoxycarbonylamino)piperidine

Product 1

HCID 698308014-Amino-1-(1-benzyloxycarbonyl-4-piperidinylmethyl)piperidineYield 101.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 1-(1-benzyloxycarbonyl-4-piperidinylmethyl)-4-(t-butoxycarbonylamino)piperidine (7.77 g) in ethanol (30 ml) is added a 30% solution of hydrochloric acid in ethanol (15 ml) under ice-cooling, and the mixture is stirred at room temperature for 5 hours. The solvent is evaporated under reduced pressure, and the residue is dissolved in water. The solution is basified with potassium carbonate and extracted with chloroform. The extract is washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure to give the desired compound (6.04 g) as an oily product.

Workup

  1. temperaturecooling
  2. customThe solvent is evaporated under reduced pressure
  3. dissolutionthe residue is dissolved in water
  4. extractionextracted with chloroform
  5. washThe extract is washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-7b9c5f06f1bc45fa965ecc36c4a14056
Source dataset
uspto-grants-2001_09
Patent number
US06294555B1

Reaction notes

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