Ammonia → HCID 22380566, compound

HRID 895642Notes

Reaction equation

HRID 895642 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:16]3[C:17]([CH3:21])=[CH:18][CH:19]=[CH:20][C:15]=3[NH:14][C:13]2=O)[CH2:8][CH2:7]1)=O)C.[CH2:23]([O:25]C(N1CCC(C(C(OCC)=O)N)(C2C=CC=CC=2C)CC1)=O)C.C(O)(=O)CO.N>Cl>[OH:25][CH2:23][C:13]1[N:12]([CH:9]2[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]2)[C:16]2[C:17]([CH3:21])=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 757Glycolic AcidHCID 22380577HCID 22380577, compoundHCID 69719582HCID 69719582, compound

Product 1

HCID 22380566HCID 22380566, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

The 1-Ethoxycarbonyl-4-(1,3-dihydro-7-methyl-2H-benzimidazol-2-on-1-yl)piperidine (40 mg) obtained in Reference Example 11, (d) was dissolved in 5 N aqueous hydrochloric acid (0.8 ml), added with glycolic acid (16 mg) and stirred at 100° C. for 3 days. The reaction mixture was made alkaline by addition of aqueous ammonia and extracted twice with dichloromethane (2 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain 14.4 mg of the title compound. Yield: 41%.

Workup

  1. extractionextracted twice with dichloromethane (2 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-985121501c2649ddbede66f6323d8c3e
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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