Sodium Hydroxide → HCID 67829404, compound

HRID 1885354Notes

Reaction equation

HRID 1885354 reaction equation
[O:1]=[C:2]1[N:7]2[CH2:8][C:9]3[C:14]([C:6]2=[C:5]([C:15]([NH:17][CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)=[O:16])[CH:4]=[C:3]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[OH-].[Na+]>FC(F)(F)C(O)=O>[NH2:20][CH2:19][CH2:18][NH:17][C:15]([C:5]1[C:6]2=[C:14]3[C:9](=[CH:8][N:7]2[C:2](=[O:1])[CH:3]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:4]=1)[CH:10]=[CH:11][CH:12]=[CH:13]3)=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86746106HCID 86746106, compound

Product 1

HCID 67829404HCID 67829404, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A suspension of 0.9 g of tert.-butyl [2-(4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxamido)ethyl]carbamate in 1.6 ml of trifluoroacetic acid was stirred at room temperature. The reaction was finished after about 15 minutes and the reaction mixture was treated slowly with 36 ml of 0.25N sodium hydroxide solution, whereby the product crystallized out. The product was stirred for a short time and then filtered off under suction. After chromatography on silica gel with methylene chloride/methanol (9:1 and 2:1) and recrystallization from methanol there was obtained 0.31 g of N-(2-aminoethyl)-4,5-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxamide with a m.p. of 216°-218°.

Workup

  1. customcrystallized out
  2. stirringThe product was stirred for a short time
  3. filtrationfiltered off under suction
  4. customAfter chromatography on silica gel with methylene chloride/methanol (9:1 and 2:1) and recrystallization from methanol

Sources & evidence

ORD record
ord-78dc3be642b640f8aac5a66643cd45ec
Source dataset
uspto-grants-1992_09
Patent number
US05143912

Reaction notes

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