Methylamine → HCID 21910602, compound

HRID 1245285Notes

Reaction equation

HRID 1245285 reaction equation
Br[CH2:2][C:3]1[C:7]2([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[NH:6][S:5](=[O:14])(=[O:13])[C:4]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1.[CH3:22][NH2:23]>C(O)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:4]2[S:5](=[O:14])(=[O:13])[NH:6][C:7]3([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]3)[C:3]=2[CH2:2][NH:23][CH3:22])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 21910636HCID 21910636, compound

Product 1

HCID 21910602HCID 21910602, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Bromomethyl-3-(4-chlorophenyl)-2-thia-1-azaspiro[4.5]dec-3-ene 2,2-dioxide, made as described in Example 2, (270 mg, 0.69 mmol) was dissolved in ethanol (30 mL). Methylamine (70% solution in water, 8 mL) was added and the mixture was stirred overnight at room temperature and concentrated. The residue was dissolved in CH2Cl2, washed with water and extracted with 0.5 M HCl. After addition of NaOH and extraction with CH2Cl2 the organic layer was dried (Na2SO4) and evaporated to yield 80 mg (34%) of 3-(4-Chlorophenyl)-4-methylaminomethyl-2-thia-1-azaspiro[4.5]dec-3-ene 2,2-dioxide as a solid. MS (IS): 341 [MH]+

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with water
  4. extractionextracted with 0.5 M HCl
  5. additionAfter addition of NaOH and extraction with CH2Cl2 the organic layer
  6. dry with materialwas dried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-a6a46054166e47f188ff562b861fc636
Source dataset
uspto-grants-2006_10
Patent number
US07125840B2

Reaction notes

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