Butyl iodide → HCID 9910149, compound

HRID 1107396Notes

Reaction equation

HRID 1107396 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:27])[C:16]([OH:26])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]([CH3:19])[CH3:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:30](I)[CH2:31][CH2:32][CH3:33]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15](=[O:27])[C:16]([O:26][CH2:30][CH2:31][CH2:32][CH3:33])([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:17]([CH3:19])[CH3:18])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10962Butyl iodide2×HCID 24758Sodium hydrideHCID 18787250HCID 18787250, compound

Product 1

HCID 9910149HCID 9910149, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalyst2×HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of N-(1-benzyl-4-piperidinyl)-2-hydroxy-3-methyl-2-phenylbutanamide (20.0 g) in DMF (200 ml) was added sodium hydride (9.0 g). The resulting mixture was stirred at room temperature for one hour, followed by the dropwise addition of butyl iodide (8.3 ml) and a solution of tetra-n-butylammonium iodide (1.8 g) in DMF (30 ml) under ice cooling. Two hours later, butyl iodide (8.3 ml) and a solution of tetra-n-butylammonium iodide (1.8 g) in DMF (30 ml) were added dropwise again over 15 minutes under ice cooling, followed by stirring overnight at room temperature. The reaction mixture was poured into ice water (500 ml). The mixture was extracted with ethyl acetate (300 ml×2) to separate the organic layer. The organic layer so obtained was washed with water and dried over anhydrous sodium sulfate. The solvent was then removed under pressure. To the residue, 100 ml of ether and 100 ml of hexane were added. After the starting materials so precipitated were filtered off, the solvent was removed under reduced pressure. The residue was purified by a silica gel column to obtain the invention compound (Compound No. 4, 6.50 g, 28.2%) as a colorless oil.

Workup

  1. stirringby stirring overnight at room temperature
  2. extractionThe mixture was extracted with ethyl acetate (300 ml×2)
  3. customto separate the organic layer
  4. customThe organic layer so obtained
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was then removed under pressure
  8. additionTo the residue, 100 ml of ether and 100 ml of hexane were added
  9. customAfter the starting materials so precipitated
  10. filtrationwere filtered off
  11. customthe solvent was removed under reduced pressure
  12. customThe residue was purified by a silica gel column
  13. customto obtain the invention compound (Compound No. 4, 6.50 g, 28.2%) as a colorless oil

Sources & evidence

ORD record
ord-5de7f9f05d014dee99e2641ef422a9c8
Source dataset
uspto-grants-2000_05
Patent number
US06060485

Reaction notes

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