p-Bromobenzenesulfonyl chloride → HCID 178483911, compound

HRID 1063629Notes

Reaction equation

HRID 1063629 reaction equation
Cl.[OH:2][CH2:3][CH2:4][CH2:5][N:6]([CH3:20])[C:7](=[O:19])[CH2:8][CH2:9][O:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([NH:17][CH3:18])[CH2:13][CH2:12]1.C(N(CC)C(C)C)(C)C.[Br:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(Cl)Cl>[Br:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([N:17]([CH3:18])[C@H:14]2[CH2:13][CH2:12][C@H:11]([O:10][CH2:9][CH2:8][C:7]([N:6]([CH2:5][CH2:4][CH2:3][OH:2])[CH3:20])=[O:19])[CH2:16][CH2:15]2)(=[O:39])=[O:38])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178484856HCID 178484856, compound

Product 1

HCID 178483911HCID 178483911, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 158 mg (0.5 mmol) of trans-N-(3-hydroxy-propyl)-N-methyl-3-(4-methylamino-cyclohexyloxy)-propionamide-hydrochloride in 3 mL of CH2Cl2 were added 0.44 mL (2.6 mmol, 5 eq) of N,N-diisopropylethylamine followed by 0.14 mg (0.56 mmol, 1.1 eq) of 4-bromo-benzenesulfonyl chloride. The mixture was stirred at RT for 1 h and the organic phase was extracted with 1M KHSO4. The combined organic phases were washed with brine, dried over Na2SO4 and evaporated. Column chromatography on silica gel with a gradient of CH2Cl2:MeOH 98:2 to 95:5 yielded 101 mg (40%) of trans-3-{4-[(4-bromo-benzenesulfonyl)-methyl-amino]-cyclohexyloxy}-N-(3-hydroxy-propyl)-N-methyl-propionamide as colorless oil, MS: 491 (MH+,1Br).

Workup

  1. extractionthe organic phase was extracted with 1M KHSO4
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-b6ff60b9ec3d41cca07d381a18091763
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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