Hydrochloric Acid → HCID 19867696, compound

HRID 1199046Notes

Reaction equation

HRID 1199046 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[N:3]1[CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[H-].[Na+].[Cl:16][CH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:26])[N:18]1[C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[N:30][C:31]([Cl:37])=[CH:32][CH:33]=2)[N:28]=1.Cl>O1CCCC1.O.C(OCC)(=O)C>[ClH:16].[Cl:37][C:31]1[N:30]=[C:29]2[C:34]([CH:35]=[CH:36][C:27]([N:18]3[CH:17]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][N:3]4[CH:4]([CH3:8])[CH2:5][CH2:6][CH2:7][CH:2]4[CH3:1])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]3=[O:26])=[N:28]2)=[CH:33][CH:32]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinoneHCID 19867661HCID 19867661, compound

Product 1

HCID 19867696HCID 19867696, compoundYield 11.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The procedure is as in Example 7, but starting with 4-(2,6-dimethyl-1-piperidyl)butanol (8 g) in anhydrous tetrahydrofuran (220 cc), an oily suspension (50% by weight; 1.9 g) of sodium hydride and 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (8.6 g). The residue obtained is taken up with ethyl acetate (20 cc); the insoluble product is removed by filtration and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residue obtained is taken up with water (50 cc) and 4N aqueous hydrochloric acid solution (20 cc); the remaining insoluble product is removed by filtration. The filtrate is neutralized with 4 N aqueous sodium hydroxide solution and then extracted with methylene chloride (3×100 cc); the organic extracts are combined and washed with water, dried and concentrated to dryness under reduced pressure (3 kPa) at 40° C. The residue obtained is recrystallized successively in ethyl acetate and 2-propanol, and 2-(7-chloro-1,8-naphthyridin-2-yl)-3-[4-(2,6-dimethylpiperidino)butoxy]-1isoindolinone hydrochloride (1.6 g) is thereby obtained.

Workup

  1. customThe residue obtained
  2. customthe insoluble product is removed by filtration
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  4. customThe residue obtained
  5. customthe remaining insoluble product is removed by filtration
  6. extractionextracted with methylene chloride (3×100 cc)
  7. washwashed with water
  8. customdried
  9. concentrationconcentrated to dryness under reduced pressure (3 kPa) at 40° C
  10. customThe residue obtained
  11. customis recrystallized successively in ethyl acetate

Sources & evidence

ORD record
ord-369754105c594b15a396766b42360dc8
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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