Allyl chloride → HCID 14074783, compound

HRID 620894Notes

Reaction equation

HRID 620894 reaction equation
[C:1]([C:5]1[CH:23]=[CH:22][C:8]([CH2:9][NH:10][CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH2:30](Cl)[CH:31]=[CH2:32]>CN(C)C=O>[CH2:32]([N:10]([CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)[CH2:9][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:23][CH:22]=1)[CH:31]=[CH2:30]

Participants

5

Reactant 3

HCID 7850Allyl chlorideHCID 10340Sodium CarbonateHCID 149867661-(4-tert-Butylphenyl)-N-[(naphthalen-1-yl)methyl]methanamine

Product 1

HCID 14074783HCID 14074783, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.03 g (0.01 mole) of N-(4'-t-butylbenzyl)-1-naphthylmethylamine was dissolved in 50 ml of dry dimethylformamide, and 1.6 g (0.015 mole) of anhydrous sodium carbonate was added. With continued stirring at room temperature, 0.84 g (0.011 mole) of allyl chloride was added, and the mixture was reacted at 30° to 40° C. for 5 hours. The reaction mixture was mixed with ice water and extracted with toluene. The organic layer was washed with water, and toluene was evaporated. The residue was chromatographed on a silica gel column, and eluted with 5% ethyl acetate/n-hexane. The eluate was concentrated to give 3.26 g (yield 95%) of an oily substance.

Workup

  1. customthe mixture was reacted at 30° to 40° C. for 5 hours
  2. extractionextracted with toluene
  3. washThe organic layer was washed with water, and toluene
  4. customwas evaporated
  5. customThe residue was chromatographed on a silica gel column
  6. washeluted with 5% ethyl acetate/n-hexane
  7. concentrationThe eluate was concentrated
  8. customto give 3.26 g (yield 95%) of an oily substance

Sources & evidence

ORD record
ord-b5e85ffcafb643a388f9412c6b161c21
Source dataset
uspto-grants-1989_04
Patent number
US04822822

Reaction notes

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