Water → HCID 23035230, compound

HRID 1709975Notes

Reaction equation

HRID 1709975 reaction equation
[OH:1][C:2]1[C:18]([O:19][CH3:20])=[CH:17][C:5]2[S:6][C:7]([C:9]3[CH:10]([CH3:16])[CH2:11][C:12](=[O:15])[NH:13][N:14]=3)=[CH:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.O>CN(C)C=O>[CH3:20][O:19][C:18]1[C:2]([O:1][CH2:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:3][C:4]2[CH:8]=[C:7]([C:9]3[CH:10]([CH3:16])[CH2:11][C:12](=[O:15])[NH:13][N:14]=3)[S:6][C:5]=2[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 79624N-(3-chloropropyl)piperidine hydrochloride2×HCID 23035245HCID 23035245, compound

Product 1

HCID 23035230HCID 23035230, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4,5-dihydro-6-(5-hydroxy-6-methoxybenzo[b]thien-2-yl)-5-methyl-3(2H)-pyridazinone (1.0 g), anhydrous potassium carbonate (1.0 g) and 1-(3-chloropropyl)piperidine hydrochloride (0.72 g) in dimethyl formamide (12 ml) was stirred at room temperature for 3 days. The mixture was then warmed to 65° C. and, after a further 2 hours, more anhydrous potassium carbonate (0.50 g) and 1-(3chloropropyl)piperidine hydrochloride (0.36 g) were added. After a further 2 hours the reaction mixture was cooled to room temperature and poured into water (60 ml). The product, which precipitated as a gum, was isolated by decantation and then crystallized from ethyl acetate to give 4,5-dihydro-6-(6-methoxy-5-[3-(piperidin-1-yl)propyloxy]-benzo[b]thien-2-yl)-5-methyl-3(2H)-pyridazinone as a white solid (0.90 g), m.p. 198°-200° C.

Workup

  1. temperatureThe mixture was then warmed to 65° C. and, after a further 2 hours
  2. temperatureAfter a further 2 hours the reaction mixture was cooled to room temperature
  3. customThe product, which precipitated as a gum
  4. customwas isolated by decantation
  5. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a14fb3bed5c147d19b57f6e5f10f5057
Source dataset
uspto-grants-1990_08
Patent number
US04952571

Reaction notes

Loading…