1-Iodopentane → HCID 9840992, compound

HRID 893278Notes

Reaction equation

HRID 893278 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][N:17]2[CH3:22])=[O:13])=[CH:4]1.I[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CN(C=O)C>[CH2:24]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][N:17]2[CH3:22])=[O:13])=[CH:4]1)[CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 123351-IodopentaneHCID 24758Sodium hydrideHCID 19891949(1-Methyl-2-piperidinyl)methyl 1H-indole-3-carboxylate

Product 1

HCID 9840992HCID 9840992, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a DMF (5 ml) suspension of 60% sodium hydride (0.10 g, 2.5 mmol) was dropwise added a DMF (7 ml) solution of (1-methyl-2-piperidyl)methyl 1H-indole-3-carboxylate (0.50 g, 1.7 mmol) at room temperature over a period of 10 min. The mixture was stirred for 45 min., onto which was then poured 1-iodopentane (0.38 g, 1.9 mmol) followed by stirring for additional 4 hours. A reaction solution was poured onto ice water followed by extraction with ethyl acetate (50 ml). The extract was washed successively with water and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give a pale yellow crude product (0.52 g). Purification of the product by column chromatography on silica gel (SiO2 : 20 g, CHCl3 /MeOH=20/1) afforded the title compound (0.33 g) as a colorless oil.

Workup

  1. stirringby stirring for additional 4 hours
  2. additionA reaction solution was poured onto ice water
  3. extractionfollowed by extraction with ethyl acetate (50 ml)
  4. washThe extract was washed successively with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto give a pale yellow crude product (0.52 g)
  8. customPurification of the product by column chromatography on silica gel (SiO2 : 20 g, CHCl3 /MeOH=20/1)

Sources & evidence

ORD record
ord-8e8d4adb4dbd4125a368247c3f0107f5
Source dataset
uspto-grants-1992_06
Patent number
US05124324

Reaction notes

Loading…