Proton sponge → HCID 19045435, compound

HRID 1781369Notes

Reaction equation

HRID 1781369 reaction equation
C[N:2]1[CH2:7][CH2:6][C:5]2([CH2:12][C:11]3[CH:13]=[CH:14][C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:16][C:10]=3[CH2:9][O:8]2)[CH2:4][CH2:3]1.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.[Cl:38]C(OC(Cl)C)=O>ClC(Cl)C>[ClH:38].[CH3:21][S:18]([NH:17][C:15]1[CH:14]=[CH:13][C:11]2[CH2:12][C:5]3([O:8][CH2:9][C:10]=2[CH:16]=1)[CH2:4][CH2:3][NH:2][CH2:7][CH2:6]3)(=[O:19])=[O:20]

Participants

5

Reactant 3

HCID 88675Proton spongeHCID 5213051-Chloroethyl chloroformateHCID 15740640HCID 15740640, compound

Product 1

HCID 19045435HCID 19045435, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1,4-dihydro-1'-methyl-7-methanesulfonamido-spiro[(3H)-2-benzopyran-3,4'-piperidine](0.575 g) and N,N,N',N'-tetramethyl-1,8-napthalenediamine (proton sponge) (0.6 g) in dichloroethane under nitrogen at 0° C. was added 1-chloroethyl chloroformate (0.613 ml). The mixture was stirred at reflux for 2 hours, cooled filtered through silca gel (20 g) and the product eluted with ethyl acetate. The eluate was concentrated and the residue dissolved in methanol (20 ml) and refluxed for 18 hours. The reaction was concentrated to a foam and crystallized from ethanol/hexanes yielding 0.548 g of product.

Workup

  1. temperatureat reflux for 2 hours
  2. temperaturecooled
  3. filtrationfiltered through silca gel (20 g)
  4. washthe product eluted with ethyl acetate
  5. concentrationThe eluate was concentrated
  6. dissolutionthe residue dissolved in methanol (20 ml)
  7. temperaturerefluxed for 18 hours
  8. concentrationThe reaction was concentrated to a foam
  9. customcrystallized from ethanol/hexanes yielding 0.548 g of product

Sources & evidence

ORD record
ord-929bcdee11ce49d59e2a83b23d640eb8
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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