Diethylcarbamoyl chloride → HCID 14181208, compound

HRID 1073119Notes

Reaction equation

HRID 1073119 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 1 N 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-630827cf311d43d382bf2912bb571e8f
Source dataset
uspto-grants-1990_11
Patent number
US04968679

Reaction notes

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