Dimethylformamide → 1-[3-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propoxy]benzoyl]piperidine

HRID 1731411Notes

Reaction equation

HRID 1731411 reaction equation
[H-].[Na+].CN(C)C=O.[OH:8][C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=1)[C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13].Br[CH2:24][CH2:25][CH2:26][N:27]1[C:31](=[O:32])[C:30]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]2[C:28]1=[O:37]>O>[O:37]=[C:28]1[C:29]2[C:30](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31](=[O:32])[N:27]1[CH2:26][CH2:25][CH2:24][O:8][C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=1)[C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 80730633-(1-Piperidinylcarbonyl)phenol

Product 1

HCID 137325571-[3-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propoxy]benzoyl]piperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 0.09 g. (0.0024 mole) of 60% sodium hydride in 10 ml. of dry N,N-dimethylformamide is added dropwise over 5 minutes a solution of 0.5 g. (0.0024 mole) of 1-(3-hydroxybenzoyl)piperidine, prepared according to the method of G. Tilly, Chem. Ther. 2 (1), 57-65 (1967); C. A. 67 32432S, in 10 ml. of dry N,N-dimethylformamide. The mixture is stirred at room temperature for 5 minutes and then 0.64 g. (0.0024 mole) of N-(3-bromopropyl)phthalimide is added. The mixture is stirred at room temperature for 1 hour and is diluted with water to the cloudy point. The precipitate which forms is collected and is air dried to give 0.5 g. of product. A small amount is recrystallized from ethanol to give the analytical sample, m.p. 120°-122° C.

Workup

  1. additionTo a suspension of 0.09 g
  2. stirringThe mixture is stirred at room temperature for 1 hour
  3. customThe precipitate which forms is collected
  4. customdried
  5. customto give 0.5 g
  6. customA small amount is recrystallized from ethanol
  7. customto give the analytical sample, m.p. 120°-122° C.

Sources & evidence

ORD record
ord-1aa3be5bcea3439e92e8ab64922f7c91
Source dataset
uspto-grants-1986_11
Patent number
US04621142

Reaction notes

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