Hydrochloric Acid → HCID 21936747, compound

HRID 2188002Notes

Reaction equation

HRID 2188002 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11](=[O:30])[N:12]([CH2:19][CH:20]1[NH:29][CH2:28][CH2:27][C:22]3(OCC[O:23]3)[CH2:21]1)[C:13]2=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11](=[O:30])[N:12]([CH2:19][CH:20]1[CH2:21][C:22](=[O:23])[CH2:27][CH2:28][NH:29]1)[C:13]2=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21936760HCID 21936760, compound

Product 1

HCID 21936747HCID 21936747, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of the above 4-benzyloxy-2-(1,4-dioxa-8-aza-spiro[4.5]dec-7-ylmethyl)-isoindole-1,3-dione (0.22 g, 0.54 mmol) in 1,4-dioxane (4 ml) was added 4N hydrochloric acid (4 ml) and the reaction stirred in a 65° C. (oil bath) for 6 hours. The mixture was basified with saturated sodium bicarbonate until pH=8 and extracted with dichloromethane (3×20 ml). The combined organic extracts were dried (MgSO4), filtered, and the solvent evaporated in vacuo affording crude 4-benzyloxy-2-(4-oxo-piperidin-2-ylmethyl)-isoindole-1,3-dione as an oil. Which was used without further purification or characterization.

Workup

  1. extractionextracted with dichloromethane (3×20 ml)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-f1f009d2fd124a05b92d4f5a94e93820
Source dataset
uspto-grants-2002_06
Patent number
US06410556B1

Reaction notes

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