Sodium Hydroxide → HCID 67829404, compound

HRID 256692Notes

Reaction equation

HRID 256692 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-2c8e3296c713479290d85d6cc034a843
Source dataset
uspto-grants-1993_11
Patent number
US05258387

Reaction notes

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