Hydrochloric Acid → trans-4-(Benzyl-methyl-amino)-piperidine-3-carboxylic Acid Ethyl Ester Dihydrochloride
Reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[C@H:11]([N:12]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:13])[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]1)=[O:5])[CH3:2].[ClH:28]>C(OCC)(=O)C.O1CCOCC1>[ClH:28].[ClH:28].[CH2:1]([O:3][C:4]([C@H:6]1[C@H:11]([N:12]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH3:13])[CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of trans-4-(benzyl-methyl-amino)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (235 mg, 624 μmol) in ethyl acetate (2 mL) was stirred on an ice bath and treated with 4.0 N hydrogen chloride in dioxane (6 mL). The bath was removed, and the mixture was stirred at room temperature for 18 hours. The mixture was then concentrated under vacuum, and the residue was stirred in ether, and the ether was decanted. The ether treatment was repeated twice more, and the residue was dried under vacuum to provide a white powder (231 mg) which was used without purification. 1H NMR (300 MHz, methanol-d4) δ7.60 (m, 2H), 7.54 (m, 3H), 4.6-3.8 (m, 6H), 3.68 (m, 2H), 3.4-3.0 (m, 2H), 2.90 (s, 3H), 2.52 (m, 1H), 2.28 (m, 1H), 1.35 (m, 3H).
Workup
- customThe bath was removed
- concentrationThe mixture was then concentrated under vacuum
- stirringthe residue was stirred in ether
- customthe ether was decanted
- customthe residue was dried under vacuum
Sources & evidence
- ORD record
- ord-353c93d8e12943ca9d431880455dea51
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06919356B2
Reaction notes
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