Methanesulfonyl chloride → 1,2-Dihydro-1'-methyl-1-(methylsulfonyl)-spiro[3H-indole-3,4'-piperidine]

HRID 1586392Notes

Reaction equation

HRID 1586392 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)[CH2:4][CH2:3]1.[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:17]([CH3:16])(=[O:19])=[O:18])[CH2:8]2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 128015871'-Methylspiro[indoline-3,4'-piperidine]

Product 1

HCID 212167761,2-Dihydro-1'-methyl-1-(methylsulfonyl)-spiro[3H-indole-3,4'-piperidine]Yield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 1,2-dihydro-1'-methyl-spiro[3H-indole-3,4'-piperidine] (3.0 g, 14.8 mmoles) in dry CH2Cl2 (25 ml) and cool under N2 in an ice bath. Add, dropwise, methane sulfonyl chloride (1.5 ml, 19.3 mmoles), followed by ethyl diisopropyl amine (5.0 ml, 28.7 mmoles). Warm to room temperature and stir overnight. Dilute the solution to 100 ml with CH2Cl2. Wash the solution with saturated aqueous NaHCO3 (4×25 ml), then with water. Dry solution with anhydrous Na2SO4, then remove the solvent using reduced pressure. Purify the resulting reaction mixture by flash chromatography (SiO2) using 5% MeOH(NH3)/EtOAc as eluent. Yield: 3.37 g (81%) of the title compound.

Workup

  1. temperaturecool under N2 in an ice bath
  2. additionAdd
  3. washWash the solution with saturated aqueous NaHCO3 (4×25 ml)
  4. customDry solution with anhydrous Na2SO4, then remove the solvent
  5. customPurify
  6. customthe resulting reaction mixture by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-c34f1553a97a4733a75facc5ee41f231
Source dataset
uspto-grants-1999_08
Patent number
US05945428

Reaction notes

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