Potassium Carbonate → HCID 19824918, compound

HRID 1084723Notes

Reaction equation

HRID 1084723 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-9ae46706fed84703acefe9190dd1dc84
Source dataset
uspto-grants-1991_04
Patent number
US05006531

Reaction notes

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