Hydrochloric Acid → HCID 68515946, compound

HRID 2266774Notes

Reaction equation

HRID 2266774 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:9][C:10]([OH:12])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[OH2:13].C(N(C(C)C)CC)(C)C.[ClH:23].O1C[CH2:28][O:27][CH2:26]C1>C(OCC)(=O)C>[Cl:23][CH2:26][O:27][C:28]([NH:1][CH2:2][C:3]1([CH2:9][C:10]([OH:12])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=[O:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3446GabapentinHCID 312751,4-Dioxane2×HCID 81531Diisopropylethylamine

Product 1

HCID 68515946HCID 68515946, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(aminomethyl)cyclohexaneacetic acid (gabapentin, 2.00 g, 11.68 mmol) in a water (30 ml) and dioxane (20 ml) mixture, diisopropylethylamine was added (4.06 ml, 23.36 mmol). In the solution thus obtained, and cooled in a water/ice bath, chloromethyl chloroformiate (1.25 ml, 14.02 mmol) dissolved in dioxane (20 ml) was slowly dropped. At the end of adding, the mixture was allowed to stand 3 hours at room temperature. The mixture was then poured in a 4% hydrochloric acid solution to sink the end pH value to about 2. Ethyl acetate was added and the organic phase<was dried under vacuum to give 2.87 g of a clear, yellow oil that was employed in the next reaction without further purification.

Workup

  1. customIn the solution thus obtained
  2. temperaturecooled in a water/ice bath
  3. additionwas slowly dropped
  4. additionAt the end of adding
  5. customthe organic phase<was dried under vacuum
  6. customto give 2.87 g of a clear, yellow oil that
  7. customwas employed in the next reaction without further purification

Sources & evidence

ORD record
ord-69dafaef3c3643df80d11ee545fb46ab
Source dataset
uspto-grants-2010_12
Patent number
US07858665B2

Reaction notes

Loading…