Hydrochloric Acid → HCID 15870800, compound

HRID 1584134Notes

Reaction equation

HRID 1584134 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])[CH:5]=[CH:4][C:3]=1[NH:14][C:15](=[O:35])[C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]2)=[CH:18][CH:17]=1.Cl>CCOC(C)=O>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])[CH:5]=[CH:4][C:3]=1[NH:14][C:15](=[O:35])[C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15870809HCID 15870809, compound

Product 1

HCID 15870800HCID 15870800, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 200 mL round bottomed flask with a stirring bar and a gas dispersion tube was added N-(2-methyl-4-(2-(N,N-dimethylamino)ethoxy)phenyl)-4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)benzamide (0.295 g, 0.61 mmol) and 50 mL of dry EtOAc. This well stirred solution was cooled in an ice bath and saturated with HCl gas over 15 min. The mixture was aged 1 h at 0° C. and the excess HCl was then removed with a stream of argon. The EtOAc was removed in vacuo and the crude product was partitioned between EtOAc and NaHCO3 solution. The layers were separated, the organic phase was washed with brine and dried (MgSO4). Filtration, removal of the solvent in vacuo and recrystallization from EtOAc gave 0.145 g of N-(2-methyl-4-(2-(N,N-dimethyl)aminoethoxy)phenyl)-4-(1-piperazinyl)benzamide, as a white crystals. mp: 139-141° C. 1H NMR (CDCl3): d 1.66 (br s, 1H), 2.28 (s, 3H), 2.33 (s, 6H), 2.72 (t, j=6 Hz, 2H), 3.05 (m, 4H), 3.27 (m, 4H), 4.05 (t, j=6 Hz, 2H), 6.77 (m, 2H), 6.93 (d, j=9 Hz, 2H), 7.45 (s, 1H), 7.63 (d, j=9 Hz, 1H), 7.77 (d, j=9 Hz, 2H).

Workup

  1. customthe excess HCl was then removed with a stream of argon
  2. customThe EtOAc was removed in vacuo
  3. customthe crude product was partitioned between EtOAc and NaHCO3 solution
  4. customThe layers were separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration, removal of the solvent
  8. customin vacuo and recrystallization from EtOAc

Sources & evidence

ORD record
ord-4d5d7d28d8a14ef3b36056965275e7cb
Source dataset
uspto-grants-1999_08
Patent number
US05932582

Reaction notes

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