4-(Trifluoromethyl)benzenesulfonyl chloride → HCID 86626020, compound

HRID 870366Notes

Reaction equation

HRID 870366 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:14][C@@H:13]3[C@H:8]([CH2:9][CH2:10][CH2:11][N:12]3[C:15](=[O:18])[CH2:16][CH3:17])[CH2:7][C:6]=2[CH:19]=1.NC1C=CC2C[C@@H]3[C@@H](CC=2C=1)N(C(=O)CC)CCC3.[F:39][C:40]([F:52])([F:51])[C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1>N1C=CC=CC=1>[F:52][C:40]([F:39])([F:51])[C:41]1[CH:42]=[CH:43][C:44]([S:47]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[CH2:14][C@@H:13]4[C@H:8]([CH2:9][CH2:10][CH2:11][N:12]4[C:15](=[O:18])[CH2:16][CH3:17])[CH2:7][C:6]=3[CH:19]=2)(=[O:49])=[O:48])=[CH:45][CH:46]=1

Participants

5

Reactant 3

HCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 86626018HCID 86626018, compoundHCID 86626021HCID 86626021, compound

Product 1

HCID 86626020HCID 86626020, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.792 g (3.065 mmol) of a 1:1 mixture trans-(7-amino-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-1-yl)-propan-1-one and trans-(8-amino-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-1-yl)-propan-1-one were dissolved in 20 ml pyridine. At 0-4° C., 0.75 g of 4-trifluoromethyl-benzene sulfonylchloride (3.066 mmol) were added, and the reaction stirred for 2 h under cooling. Pyridine was evaporated and the residue partitioned between 20% aqueous citric acid and diethylether. The aqueous layer was extracted twice with diethylether, the combined organic phases washed with 20% aqueous citric acid, dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to yield 1.327 g of the product. MSD: 467.1 g/mol

Workup

  1. temperatureunder cooling
  2. customPyridine was evaporated
  3. customthe residue partitioned between 20% aqueous citric acid and diethylether
  4. extractionThe aqueous layer was extracted twice with diethylether
  5. washthe combined organic phases washed with 20% aqueous citric acid
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-9d1acc4f99a5483a8555709007ab1c94
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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