Hydrochloric Acid → 1-(2-Methoxyethyl)piperidine-4-carboxylic acid hydrochloride

HRID 2223099Notes

Reaction equation

HRID 2223099 reaction equation
[ClH:1].C([O:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][O:15][CH3:16])[CH2:9][CH2:8]1)=[O:6])C>O>[ClH:1].[CH3:16][O:15][CH2:14][CH2:13][N:10]1[CH2:9][CH2:8][CH:7]([C:5]([OH:6])=[O:4])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21202762HCID 21202762, compound

Product 1

HCID 450750321-(2-Methoxyethyl)piperidine-4-carboxylic acid hydrochlorideYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Concentrated hydrochloric acid (200 ml) was added to a suspension of the product of Example 4 Step 1 (20 g, 93 mmol) in water (120 ml). The mixture was heated at 100° C. for 60 hours, cooled to room temperature and the solvent concentrated in vacuo. The residue was azeotroped with toluene (×5) and dried over phosphorus pentoxide. The resulting solid was triturated with diethyl ether and acetone to yield the title compound (14.0 g, 81%); MS (ES−) m/e 186 [M−H]−.

Workup

  1. temperaturecooled to room temperature
  2. concentrationthe solvent concentrated in vacuo
  3. customThe residue was azeotroped with toluene (×5)
  4. dry with materialdried over phosphorus pentoxide
  5. customThe resulting solid was triturated with diethyl ether and acetone

Sources & evidence

ORD record
ord-149512a843244560b5576b09c2d5fb78
Source dataset
uspto-grants-2008_05
Patent number
US07375105B2

Reaction notes

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