Hydrochloric Acid → 2-(1-Cyclobutylpiperidin-4-yl)acetic acid

HRID 1523721Notes

Reaction equation

HRID 1523721 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH:12]2[CH2:15][CH2:14][CH2:13]2)[CH2:8][CH2:7]1)C.O1CCCC1.O.[OH-].[Li+].Cl>O>[CH:12]1([N:9]2[CH2:8][CH2:7][CH:6]([CH2:5][C:4]([OH:16])=[O:3])[CH2:11][CH2:10]2)[CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86724910Ethyl 2-(1-cyclobutylpiperidin-4-yl)acetate

Product 1

HCID 796058692-(1-Cyclobutylpiperidin-4-yl)acetic acidYield 130.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of (1-cyclobutyl piperidin-4-yl) acetic acid ethyl ester (652.9 mg, 2.90 mmol, obtained in above step), tetrahydrofuran (6 mL) and water (6.0 mL) cooled at 0° C. lithium hydroxide monohydrate (133 mg, 3.19 mmol) was added in a single lot. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was cooled again to 0° C. and acidified with 2N hydrochloric acid to pH: 2-3. The volatiles were removed under reduced pressure and the traces of water were removed by azeotropic distillation with toluene to obtain (1-cyclobutyl piperidin-4-yl) acetic acid (747.9 mg).

Workup

  1. additionwas added in a single lot
  2. temperatureThe reaction mixture was cooled again to 0° C.
  3. customThe volatiles were removed under reduced pressure
  4. customthe traces of water were removed by azeotropic distillation with toluene

Sources & evidence

ORD record
ord-1a54a2eb879e406d9ebee0c4594506ef
Source dataset
uspto-grants-2015_07
Patent number
US09079894B2

Reaction notes

Loading…