Methylamine → HCID 23019654, compound

HRID 1354198Notes

Reaction equation

HRID 1354198 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][N:12]3[C:17]([C:18]=2[CH3:19])=[C:16]([CH:20]2[CH2:22][CH2:21]2)[CH:15]=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:13]3=[O:28])[CH:6]=[CH:7][CH:8]=1.[CH3:29][NH2:30]>O1CCCC1>[CH:20]1([C:16]2[CH:15]=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:13](=[O:28])[N:12]3[C:17]=2[C:18]([CH3:19])=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][NH:30][CH3:29])[CH:4]=2)[CH:10]=[CH:11]3)[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 23019624HCID 23019624, compound

Product 1

HCID 23019654HCID 23019654, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

31.2 mg of ethyl 8-(3-bromomethylphenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (Example 57) was dissolved in 2 ml of tetrahydrofuran. 0.1 ml of a solution of 2.0 M of methylamine in tetrahydrofuran was added to the obtained solution, and they were stirred for 10 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by the silica gel column chromatography (eluent: chloroform/methanol=5/1) to obtain 18.1 mg of ethyl 1-cyclopropyl-9-methyl-8-(3-methylaminomethylphenyl)-4-oxo-4H-quinolizine-3-carboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe obtained residue was purified by the silica gel column chromatography (eluent: chloroform/methanol=5/1)

Sources & evidence

ORD record
ord-40fabf8521174e52ad9c9ab43c06fb45
Source dataset
uspto-grants-2007_05
Patent number
US07223773B2

Reaction notes

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