Diethylcarbamoyl chloride → HCID 14181208, compound

HRID 728077Notes

Reaction equation

HRID 728077 reaction equation
[CH2:1]([N:4]([CH2:17][CH2:18][CH3:19])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([CH2:15][NH2:16])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].[CH2:20]([N:22]([CH2:26][CH3:27])[C:23](Cl)=[O:24])[CH3:21].[OH-].[Na+]>ClCCl>[CH2:17]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([CH2:15][NH:16][C:23]([N:22]([CH2:26][CH3:27])[CH2:20][CH3:21])=[O:24])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 14798Sodium HydroxideHCID 14181206HCID 14181206, compound

Product 1

HCID 14181208HCID 14181208, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.6 g (6 mmol) of 2-dipropylamino-8-aminomethyl-1,2,3,4-tetrahydronaphthalene were dissolved in 16 ml of dichloromethane under nitrogen. 0.81 g (6 mmol) of diethylcarbamoyl chloride was then added dropwise at a maximum of +25° C. The batch was then stirred for 26 h at room temperature. The batch was then stirred into 160 ml of ice water. The mixture was adjusted to pH 9 using 1N sodium hydroxide solution and extracted with dichloromethane. The organic phase was washed with water and dried over sodium sulphate. The solvent was subsequently removed by distillation. The residue was purified by column chromatography. Diisopropyl ether/isopropanol/triethylamine, 80:19.5:0.5, was used as eluent. The final product could be crystallized from petroleum ether 30-50 and was dried at +40° C. in vacuo.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic phase was washed with water
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was subsequently removed by distillation
  5. customThe residue was purified by column chromatography
  6. customThe final product could be crystallized from petroleum ether 30-50
  7. customwas dried at +40° C. in vacuo

Sources & evidence

ORD record
ord-198a7781dc97480d87920d8a9839cddc
Source dataset
uspto-grants-1991_09
Patent number
US05047422

Reaction notes

Loading…