Pyridine → HCID 56966206, compound

HRID 1036955Notes

Reaction equation

HRID 1036955 reaction equation
[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[NH:5][CH:4]([C:13]2[CH:14]=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=2)[CH2:3]1.N1C=CC=CC=1.[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[NH:5][CH:4]([C:13]2[CH:14]=[C:15]([NH:19][S:33]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:35])=[O:34])[CH:16]=[CH:17][CH:18]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 672908283-(4,4,6-Trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine

Product 1

HCID 56966206HCID 56966206, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred mixture of 3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (135 mg, 0.5 mmol) in dichloromethane (3 mL) was added pyridine (60 mg, 0.75 mmol) in dichloromethane (2 mL) and benzenesulfonylchloride (108 mg, 0.56 mmol) under nitrogen. The resultant mixture was stirred for 20 h. The reaction mixture was diluted with dichloromethane, washed with water (twice), saturated brine, and dried over magnesium sulfate. Magnesium sulfate was removed by filtration, and after evaporation, the residue was purified on chromatography column (silica gel, petroleum ether:ethyl acetate=15:1) to afford 120 mg of N-[3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-benzenesulfonamide as yellow solid (Yield: 59%). MS (ESI+APCI) M+1=407.1.

Workup

  1. washwashed with water (twice), saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customMagnesium sulfate was removed by filtration
  4. customafter evaporation
  5. customthe residue was purified on chromatography column (silica gel, petroleum ether:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-bbc50589d7fa42a0aae350fb05568816
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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