Triethylamine → N-{2-[4-(2-Chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-4-fluoro-N-methyl-benzenesulfonamide

HRID 553496Notes

Reaction equation

HRID 553496 reaction equation
C(N(CC)CC)C.Cl.[Cl:9][C:10]1[C:15]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][NH:24][CH3:25])[CH2:18][CH2:17]2)=[CH:14][CH:13]=[CH:12][N:11]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>ClCCl.C(=O)(O)[O-].[Na+]>[Cl:9][C:10]1[C:15]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][N:24]([CH3:25])[S:33]([C:30]3[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=3)(=[O:35])=[O:34])[CH2:18][CH2:17]2)=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 86640208{2-[4-(2-Chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-methyl-amine hydrochloride salt

Product 1

HCID 86640209N-{2-[4-(2-Chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-4-fluoro-N-methyl-benzenesulfonamideYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Add triethylamine (0.850 mL, 6.103 mmol) to a stirring solution of {2-[4-(2-chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-methyl-amine hydrochloride salt (2.000 g, 6.103 mmol) in dichloromethane (10 mL). Stir at room temperature for 5 min. Add 4-fluoro-benzenesulfonyl chloride (0.356 g, 1.831 mmol) at room temperature. Stir at room temperature for 18 hr. Dilute with dichloromethane and saturated aqueous sodium bicarbonate. Separate the phases and extract the aqueous phase with dichloromethane. Combine the organic phases, dry over sodium sulfate, filter, and concentrate. Purify the resulting material by silica gel chromatography eluting with hexanes:acetone 1:1 to afford the title preparation (0.525 g, 83% yield). MS ES: m/z=413 [M+H]+.

Workup

  1. customat room temperature
  2. stirringStir at room temperature for 18 hr
  3. customSeparate the phases
  4. extractionextract the aqueous phase with dichloromethane
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the resulting material by silica gel chromatography
  9. washeluting with hexanes:acetone 1:1
  10. customto afford the title
  11. custompreparation (0.525 g, 83% yield)

Sources & evidence

ORD record
ord-54539d651c06409fb3ad44fb1845c26f
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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