Methylamine → HCID 19769371, compound

HRID 1590043Notes

Reaction equation

HRID 1590043 reaction equation
[CH3:1]N.[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([N:10]2[C:19](=[O:20])[C:18]3[CH:21]=[CH:22][C:23]([N+:24]([O-])=O)=[C:16]4[C:17]=3[C:12](=[CH:13][CH:14]=[CH:15]4)[C:11]2=[O:27])[CH2:6][CH2:5]1>C(O)(C)C>[CH3:1][NH:24][C:23]1[CH:22]=[CH:21][C:18]2[C:19](=[O:20])[N:10]([CH:7]3[CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][CH2:8]3)[C:11](=[O:27])[C:12]3[C:17]=2[C:16]=1[CH:15]=[CH:14][CH:13]=3

Participants

4

Reactant 2

HCID 6329MethylamineHCID 9949784HCID 9949784, compound

Product 1

HCID 19769371HCID 19769371, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 40% aqueous methylamine (2 mL) and 2,3-dihydro-2-(1-methylpiperidin-4-yl)-6-nitro-1H-benz[de]isoquinoline-1,3-dione (1.1 g; 3.14 mmol), prepared as in Example 3, in isopropanol (10 mL) was stirred at 65°-70° C. for six hours. Concentration of the solution followed by purification of the residue by column chromatography (silica-gel; 3% methanol in CH2Cl2 and approximately 1% aqueous NH4OH) gave 2,3-dihydro-6-methyamino-2-(1-methylpiperidin-4-yl)-1H-benz[de]isoquinoline-1,3-dione (0.63 g; 1.95 mmol) as a yellow precipitate, m.p. 251°-254° C.

Workup

  1. customConcentration of the solution followed by purification of the residue by column chromatography (silica-gel; 3% methanol in CH2Cl2 and approximately 1% aqueous NH4OH)

Sources & evidence

ORD record
ord-be7aa39edfff4991a52951c816d5f29b
Source dataset
uspto-grants-1993_04
Patent number
US05202318

Reaction notes

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