Sodium Hydroxide → HCID 67829404, compound

HRID 2379587Notes

Reaction equation

HRID 2379587 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-6a485224651546d1a75a58b64a610b4f
Source dataset
uspto-grants-1994_11
Patent number
US05362738

Reaction notes

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