Hydrochloride methanol → HCID 67849835, compound

HRID 1729318Notes

Reaction equation

[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24](=[O:39])[CH:25]=[CH:26][C:27]3[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=3)[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:40])[N:4]([CH3:41])[C:3]1=[O:42].[ClH:43].CO>>[ClH:43].[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24](=[O:39])[CH:25]=[CH:26][C:27]3[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=3)[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:40])[N:4]([CH3:41])[C:3]1=[O:42]

Participants

Reactant 2

HCID 21893726Hydrochloride methanol

HCID 54248231HCID 54248231, compound

Product 1

HCID 67849835HCID 67849835, compound

Procedure

In 30 ml of anhydrous tetrahydrofuran were suspended 1.50 g of 1,3-dimethyl-6-[4-(3-[2-acetylphenoxy)propyl)-piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound 17) obtained in Example 2 and 0.7 g of 3,4,5-trimethoxybenzaidehyde, and 0.19 ml of sodium hydride (60% and oily) was added to the suspension under ice cooling. Afterward, the suspension was stirred at the same temperature for 1 hour, and 1.0 ml of anhydrous ethanol was then added dropwise thereto, followed by stirring at room temperature for 3 hours. Next, 1 ml of water was added to the reaction solution, and this solution was then concentrated to dryness under reduced pressure and the resultant residue was dissolved in 50 ml of chloroform. The chloroform solution was washed with an aqueous saturated sodium chloride solution and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified through a silica gel column chromatograph (chloroform/methanol=50/1 to 10/1 in volume ratio), thereby obtaining 1.65 g of crystalline 1,3-dimethyl-6-[4-(3-[2-(3,4,5-trimethoxycinnamoyl)phenoxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione. Furthermore, this pyrimidinedione derivative was treated with a hydrochloric acid/methanol solution in an ordinary manner to obtain the crystals of 1,3-dimethyl-6-[4-(3-[2-(3,4,5-trimethoxycinnamoyl)phenoxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.hydrochloride (Compound 145).

Sources & evidence

ORD record: ord-98cc68a12953450e8b2a4cf76278ddcf
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05332739

Reaction notes

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