Benzenesulfonyl chloride → 8-Benzenesulfonyl-1,3-dibenzyl-1,4,8-triazaspiro[4,5]decan-2-one

HRID 227257Notes

Reaction equation

HRID 227257 reaction equation
C(N(CC)CC)C.[C:8]1([S:14](Cl)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:18]([N:25]1[C:29]2([CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[NH:28][CH:27]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:26]1=[O:42])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[C:8]1([S:14]([N:32]2[CH2:33][CH2:34][C:29]3([N:25]([CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:26](=[O:42])[CH:27]([CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[NH:28]3)[CH2:30][CH2:31]2)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 688379421,3-Dibenzyl-1,4,8-triazaspiro[4,5]decan-2-one

Product 1

HCID 688387798-Benzenesulfonyl-1,3-dibenzyl-1,4,8-triazaspiro[4,5]decan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.12 ml, 0.89 mmol) and subsequently benzenesulfonyl chloride (0.19 ml, 0.26 mmol) were added to a solution of 1,3-dibenzyl-1,4,8-triazaspiro-[4,5]decan-2-one (250 mg, 0.75 mmol) in CH2Cl2 (6.7 ml) with stirring under a blanket of nitrogen at RT. The reaction mixture was stirred overnight. The organic phase was rendered alkaline using saturated aqueous sodium carbonate solution (20 ml), and the aqueous phase was extracted with CH2Cl2 (15 ml). The combined organic phases were dried over Na2SO4. After filtration, removal of the solvent, and column chromatography, the desired product 8-benzenesulfonyl-1,3-dibenzyl-1,4,8-triazaspiro[4,5]decan-2-one was obtained in a yield of 259 mg (73% of theory).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. extractionthe aqueous phase was extracted with CH2Cl2 (15 ml)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationAfter filtration, removal of the solvent, and column chromatography

Sources & evidence

ORD record
ord-86dfa6d6cd3f4ebcbc8f44c528aa1d8b
Source dataset
uspto-grants-2009_07
Patent number
US07560468B2

Reaction notes

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