Proton sponge → HCID 19045570, compound

HRID 1591214Notes

Reaction equation

HRID 1591214 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[C:9]1([CH2:14][CH2:13][N:12](C)[CH2:11][CH2:10]1)[NH:8][CH2:7][C:6]2=[O:21].CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.[Cl:38]C(OC(Cl)C)=O>ClC(Cl)C>[ClH:38].[ClH:38].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[C:9]1([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[NH:8][CH2:7][C:6]2=[O:21]

Participants

5

Reactant 3

HCID 88675Proton spongeHCID 5213051-Chloroethyl chloroformateHCID 19045317HCID 19045317, compound

Product 1

HCID 19045570HCID 19045570, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 6,7-dimethoxy-1'-methylspiro[1,2,3,4-tetrahydroisoquinoline-1,4'-piperidin]-4-one (Helv. Chem. Acta., 58, Fasc. 1, Nr. 8 (1975)) (1.0 g) and N,N,N',N'-tetramethyl-1,8-napthalenediamine (1.9 g) in dichloroethane at 0° C. under nitrogen was added 1-chloroethyl chloroformate (9.5 ml) and the mixture stirred at reflux for 1 hr. The reaction was cooled, passed thru silica and the product eluted with 10% ethyl acetate in methylene chloride. After evaporation, methanol was added and the mixture refluxed for 1 hr. Upon evaporation the foam was crystallized from ethanol/ether to give 0.6 g of the title compound as dihydrochloride salt.

Workup

  1. temperatureat reflux for 1 hr
  2. temperatureThe reaction was cooled
  3. washthe product eluted with 10% ethyl acetate in methylene chloride
  4. customAfter evaporation, methanol
  5. additionwas added
  6. temperaturethe mixture refluxed for 1 hr
  7. customUpon evaporation the foam
  8. customwas crystallized from ethanol/ether

Sources & evidence

ORD record
ord-fded702d0edd4cdaa6bd65f3b5cb4b9d
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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