Hydrochloric Acid → 1-(Tert-butoxycarbonyl)-4-(2-(dimethylamino)ethyl)piperidine-4-carboxylic acid

HRID 216073Notes

Reaction equation

HRID 216073 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][C:5]1([C:18]([O:20]CC)=[O:19])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.O.[OH-].[Li+].CCO.Cl>O>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C:5]([CH2:4][CH2:3][N:2]([CH3:23])[CH3:1])([C:18]([OH:20])=[O:19])[CH2:6][CH2:7]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 67036842HCID 67036842, compound

Product 1

HCID 670368571-(Tert-butoxycarbonyl)-4-(2-(dimethylamino)ethyl)piperidine-4-carboxylic acidYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-tert-Butyl 4-ethyl 4-(2-(dimethylamino)ethyl)piperidine-1,4-dicarboxylate from step A (328 mg, 1.0 mmol) was treated overnight with lithium hydroxide monohydrate (210 mg, 5 mmol) in 1:1 EtOH:H2O (5 mL) at 60° C. The reaction was cooled to room temperature, neutralized to pH 6 with 1 N aq. HCl, and concentrated under vacuum. The residue was purified by prep HPLC and lyophilized twice to give the title compound (191 mg, 64%) as a white solid. MS (ES+) [M+H]+=301.

Workup

  1. customat 60° C
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-3e83e6bfc9a24a7fa1acf34addaaada1
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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