Ethylamine → HCID 21910637, compound

HRID 1245290Notes

Reaction equation

HRID 1245290 reaction equation
Br[CH2:2][C:3]1[C:7]2([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[NH:6][C:5](=[O:13])[C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.[CH2:22]([NH2:24])[CH3:23]>C(O)C>[CH2:22]([NH:24][CH2:2][C:3]1[C:7]2([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[NH:6][C:5](=[O:13])[C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH3:23]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 21910676HCID 21910676, compound

Product 1

HCID 21910637HCID 21910637, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Bromomethyl-3-(4-methoxyphenyl)-1-azaspiro[4.5]dec-3-ene-2-one (250 mg, 0.71 mmol) was dissolved in ethanol (15 mL) and ethylamine (70% solution in water, 2 mL), 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 0.22 g (98%)of 4-ethylaminomethyl-3-(4-methoxyphenyl)-1-azaspiro[4.5]dec-3-ene-2-one, shown below, as a solid. MS (IS): 315 [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-1597b4d0ae2f4ceab6ea75988d034678
Source dataset
uspto-grants-2006_10
Patent number
US07125840B2

Reaction notes

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