1-Methylpiperazine → 1',3,3'-Trimethyl-2,3,4,4a-tetrahydro-1H,2'H,6H-spiro[pyrazino[1,2-a]quinoline-5,5'-pyrimidine]-2',4',6'(1'H,3'H)-trione

HRID 1271900Notes

Reaction equation

HRID 1271900 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[CH3:17][N:18]1[C:25](=[O:26])[CH2:24][C:22](=[O:23])[N:21]([CH3:27])[C:19]1=[O:20]>>[CH3:27][N:21]1[C:22](=[O:23])[C:24]2([CH2:4][C:3]3[C:2](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:14]3[CH2:13][CH2:12][N:11]([CH3:10])[CH2:16][CH:15]23)[C:25](=[O:26])[N:18]([CH3:17])[C:19]1=[O:20]

Participants

4

Reactant 3

HCID 531671-MethylpiperazineHCID 67970o-FluorobenzaldehydeHCID 69860Dimethylbarbituric acid

Product 1

HCID 34306871',3,3'-Trimethyl-2,3,4,4a-tetrahydro-1H,2'H,6H-spiro[pyrazino[1,2-a]quinoline-5,5'-pyrimidine]-2',4',6'(1'H,3'H)-trioneYield 55%

Procedure

In a manner similar to that described in Example 1, except starting with 2-fluorobenzaldehyde, 1-methylpiperazine and 1,3-dimethylbarbituric acid, 190 mg (55%) of the title compound is obtained. 1H NMR (400 MHz, CDCl3) δ 7.19, 7.04, 6.95, 6.80, 3.98, 3.62, 3.55, 3.39, 3.32, 3.10, 3.04, 2.82, 2.57, 2.23, 2.21, 1.86.

Sources & evidence

ORD record
ord-c97ea29f05d54aa19613e8b87e7c0207
Source dataset
uspto-grants-2007_04
Patent number
US07208490B2

Reaction notes

Loading…