Sodium hydride → HCID 23363844, compound

HRID 1081278Notes

Reaction equation

HRID 1081278 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[O:15][CH2:14][CH2:13][O:12]1.[H-].[Na+].Cl.Cl[CH2:20][CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24][CH2:23]1>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:20][CH2:21][CH:22]1[CH2:23][CH2:24][N:25]([CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:26][CH2:27]1)[C:6](=[O:11])[C:5]12[O:12][CH2:13][CH2:14][O:15]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3732509HCID 3732509, compoundHCID 675574611-Benzyl-4-(2-chloroethyl)piperidine--hydrogen chloride (1/1)

Product 1

HCID 23363844HCID 23363844, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
80 °C

Procedure

5'-Methyl-spiro[1,3-dioxolane-2,3'-[3H]indol]-2'(1'H)-one (1 equivalent) in dry DMF (5 ml) was added dropwise to sodium hydride (3 equivalents) in dry DMF (2 ml) at 0° C. After 20 minutes, a solution of 4-(2-chloroethyl)-1-(phenylmethyl)piperidine hydrochloride (1.5 equivalents) in dry DMF (15 ml) was slowly added. The mixture was heated to 80° C., stirred at this temperature for 3 hours, and then left at RT overnight. The mixture was evaporated to dryness under reduced pressure and the residue purified by flash chromatography to yield the title compound (53%).

Workup

  1. waitleft at RT overnight
  2. customThe mixture was evaporated to dryness under reduced pressure
  3. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-779ae0df8f3144679b3e78d8bdbca335
Source dataset
uspto-grants-1996_12
Patent number
US05585378

Reaction notes

Loading…