Triethylamine → HCID 86590430, compound

HRID 1986966Notes

Reaction equation

HRID 1986966 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[CH:5][C:6]2[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]4[CH2:20][C@H:19]4[CH2:21][OH:22])[CH2:13][CH2:12]3)=[CH:9][S:8][C:7]=2[CH:23]=1.CCN(CC)CC.[CH3:33][S:34](Cl)(=[O:36])=[O:35].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.O>[F:25][C:2]([F:24])([F:1])[C:3]1[CH:4]=[CH:5][C:6]2[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]4[CH2:20][C@H:19]4[CH2:21][O:22][S:34]([CH3:33])(=[O:36])=[O:35])[CH2:13][CH2:12]3)=[CH:9][S:8][C:7]=2[CH:23]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 68994515HCID 68994515, compound

Product 1

HCID 86590430HCID 86590430, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of {(1R, 2R)-2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-ylmethyl]-cyclopropyl}-methanol (3.712 g, 10.03 mmol) in Et3N (8.5 mL, 61.1 mmol) and anhydrous CH2Cl2 (100 mL ) at 0° C. under N2 was added dropwise CH3SO2Cl (930 uL, 12.02 mmol ). Stirring was continued at 0° C. for 2.5 h. The reaction was quenched with H2O (20 mL). A solution of K2CO3 (4.28 g, 31.01 mmol) in H2O (60 mL) was then added. The resulting mixture was stirred at rt for 15 min, then extracted with CH2Cl2, washed with brine, dried over Na2SO4. Filtration, concentration and drying afforded the desired product (4.301 g, 96%).

Workup

  1. customThe reaction was quenched with H2O (20 mL)
  2. stirringThe resulting mixture was stirred at rt for 15 min
  3. extractionextracted with CH2Cl2
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration, concentration
  7. customdrying

Sources & evidence

ORD record
ord-9a18120140bc4bf185a00246b00de534
Source dataset
uspto-grants-2009_06
Patent number
US07550469B2

Reaction notes

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