Dimethylamine, hydrochloride → HCID 22710951, compound

HRID 352918Notes

Reaction equation

HRID 352918 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:36])[C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][N:31]=[C:30]([CH2:34]O)[CH:29]=4)=[CH:24][CH:23]=3)[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.Cl.[CH3:38][NH:39][CH3:40].C(=O)([O-])[O-].[K+].[K+]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:16][CH2:17][N:18]([C:21](=[O:36])[C:22]3[CH:23]=[CH:24][C:25]([C:28]4[CH:33]=[CH:32][N:31]=[C:30]([CH2:34][N:39]([CH3:40])[CH3:38])[CH:29]=4)=[CH:26][CH:27]=3)[CH2:19][CH2:20]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

4

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 18628942HCID 18628942, compound

Product 1

HCID 22710951HCID 22710951, compoundYield 44%

Procedure

In the same manner as in Referential Example 178, the corresponding brome compound was obtained using 1-[(6-chloronaphthalen-2-yl)sulfonyl]-4-[4-(2-hydroxymethylpyridin-4-yl)benzoyl]piperazine (300 mg). To the resulting compound, dimethylamine hydrochloride (469 mg) and potassium carbonate (795 mg) were added, followed by stirring for 24 hours. The solvent was then distilled off under reduced pressure. Ethyl acetate and water were added to the residue to separate the organic layer. The organic layer thus obtained was dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (3 to 5% methanol—dichloromethane). Hydrochloric acid in ethanol was added and the resulting mixture was concentrated. Ethyl acetate was added to the concentrate. The colorless powder thus obtained was collected by filtration and dried, whereby the title compound (74 mg, 21%) was obtained.

Workup

  1. customIn the same manner as in Referential Example 178, the corresponding brome compound was obtained
  2. distillationThe solvent was then distilled off under reduced pressure
  3. additionEthyl acetate and water were added to the residue
  4. customto separate the organic layer
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe residue obtained
  8. distillationby distilling off the solvent under reduced pressure
  9. customwas purified by chromatography on a silica gel column (3 to 5% methanol—dichloromethane)
  10. additionHydrochloric acid in ethanol was added
  11. concentrationthe resulting mixture was concentrated
  12. additionEthyl acetate was added to the concentrate
  13. customThe colorless powder thus obtained
  14. filtrationwas collected by filtration
  15. customdried

Sources & evidence

ORD record
ord-8891c366a6a24e028053338fc5aa3313
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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