Hydrochloric Acid → Ethyl (cis-5-amino-1-benzylpiperidin-2-yl)acetate

HRID 602447Notes

Reaction equation

HRID 602447 reaction equation
[CH2:1]([N:8]1[CH2:13][C@H:12]([NH:14]C(OC(C)(C)C)=O)[CH2:11][CH2:10][C@@H:9]1[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[NH2:14][C@H:12]1[CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C@@H:9]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86624144Ethyl {cis-1-benzyl-5-[(tert-butoxycarbonyl)amino]piperidin-2-yl}acetate

Product 1

HCID 86624145Ethyl (cis-5-amino-1-benzylpiperidin-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl {cis-1-benzyl-5-[(tert-butoxycarbonyl)amino]piperidin-2-yl}acetate (2.0 g, 5.31 mmol, step 6 of Example 1) and 10% hydrochloric acid in methanol was stirred at room temperature for 20 h. The mixture was concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane/methanol (10/1, 10 mL). The solution was filtered through amine-silica gel washing with dichloromethane/methanol (10/1, 200 mL). The filtrate was concentrated under reduced pressure to give 1.65 g (quant.) of the title compound as a brown amorphous solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in dichloromethane/methanol (10/1, 10 mL)
  3. filtrationThe solution was filtered through amine-silica gel washing with dichloromethane/methanol (10/1, 200 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-682c610377ca4cdbb40f34a357057ce5
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

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