Hydrochloric Acid → HCID 15870801, compound

HRID 1584135Notes

Reaction equation

HRID 1584135 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][N:11](C(OC(C)(C)C)=O)[CH3:12])[CH:5]=[CH:4][C:3]=1[NH:20][C:21](=[O:41])[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]2)=[CH:24][CH:23]=1.Cl>CCOC(C)=O>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][NH:11][CH3:12])[CH:5]=[CH:4][C:3]=1[NH:20][C:21](=[O:41])[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21223921HCID 21223921, compound

Product 1

HCID 15870801HCID 15870801, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a 100 mL round bottomed flask with a stirring bar and a gas dispersion tube was added N-(2-methyl-4-(2-(1,1-dimethylethoxycarbonyl(methyl)amino)ethoxy)phenyl)-4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)benzamide (0.620 g, 1.09 mmol) and 40 mL of dry EtOAc. This well stirred solution was cooled to 0° C. in an ice bath and was saturated with HCl gas for over 15 min. The reaction was aged for an hour and excess HCl was removed with a stream of argon. Removal of EtOAc in vacuo and the crude HCl salt was converting to freebase by dissolving in saturated NaHCO3 solution. Extracted with EtOAc and the layers were separated. A white solid precipitated out from the aqueous and was collected via suction filtration. This crude product was recrystallized from hot MeOH-Et2O to give 0.175 g of N-(2-methyl-4-(2-methylaminoethoxy)phenyl)-4-(1-piperazinyl)benzamide as a white solid. mp: 136-137° C. 1H NMR (DMSO-d6): d 2.28 (s, 3H), 2.50 (s, 3H), 2.95 (m, 2H), 3.03 (m, 4H), 3.27 (m, 4H), 4.06 (m, 2H), 6.78 (d, j=6 Hz, 2H), 6.93 (d, j=9 Hz, 2H), 7.41 (s, 1H), 7.65 (d, j=9 Hz, 1H), 7.79 (d, j=9 Hz, 2H).

Workup

  1. waitThe reaction was aged for an hour
  2. customexcess HCl was removed with a stream of argon
  3. customRemoval of EtOAc in vacuo
  4. dissolutionby dissolving in saturated NaHCO3 solution
  5. extractionExtracted with EtOAc
  6. customthe layers were separated
  7. customA white solid precipitated out from the aqueous and
  8. filtrationwas collected via suction filtration
  9. customThis crude product was recrystallized from hot MeOH-Et2O

Sources & evidence

ORD record
ord-5ec8e0e8b7ae4c969956565aabbfce61
Source dataset
uspto-grants-1999_08
Patent number
US05932582

Reaction notes

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