Potassium Carbonate → HCID 19824918, compound

HRID 727772Notes

Reaction equation

HRID 727772 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:15]3=[C:16]4[C:21](=[N:22][C:14]3=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH2:12]3)[NH:7]2)[CH:20]=[CH:19][CH:18]=[CH:17]4)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].C[Si]([N:33]=[C:34]=[O:35])(C)C>C1COCC1>[NH2:33][C:34]([N:1]1[CH2:2][CH2:3][C:4]2([C:15]3=[C:16]4[C:21](=[N:22][C:14]3=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH2:12]3)[NH:7]2)[CH:20]=[CH:19][CH:18]=[CH:17]4)[CH2:5][CH2:6]1)=[O:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70696Trimethylsilyl isocyanateHCID 19824931HCID 19824931, compound

Product 1

HCID 19824918HCID 19824918, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4 g of 5,6-dihydrospiro[1H-indolo[3,2-c]quinoline-6,4'-piperidine] in 100 ml of THF were added 9.7 g of K2CO3 and 13.9 ml of trimethylsilyl isocyanate (32% xylene by weight). The mixture was stirred overnight at room temperature and filtered. Subsequently, an additional 5.6 ml of trimethylsilyl isocyanate was added and the resultant solution was stirred for 30 minutes at room temperature. Concentration gave a solid/gum mixture which was triturated with H2O to give 3.07 g of solid, m.p. 265°-267° dec.

Workup

  1. filtrationfiltered
  2. additionSubsequently, an additional 5.6 ml of trimethylsilyl isocyanate was added
  3. stirringthe resultant solution was stirred for 30 minutes at room temperature
  4. concentrationConcentration
  5. customgave a solid/gum mixture which
  6. customwas triturated with H2O

Sources & evidence

ORD record
ord-d287f5bf49dc43be80dc7421658d189d
Source dataset
uspto-grants-1991_09
Patent number
US05045539

Reaction notes

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