Hydrochloric Acid → Dodecylamine

HRID 1072595Notes

Reaction equation

HRID 1072595 reaction equation
C(OC(=O)N[C:8]([CH3:29])(C)[CH2:9][C:10]1[C:18]2[C:13](=[C:14](OC3C(C#N)=CC=CN=3)[CH:15]=[CH:16][CH:17]=2)[NH:12]C=1)(C)(C)C.Cl.O1CCO[CH2:34][CH2:33]1>>[CH3:33][CH2:34][CH2:29][CH2:8][CH2:9][CH2:10][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][NH2:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 69516986{2-[7-(3-cyano-pyridin-2-yloxy)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 13583DodecylamineYield 83%

Procedure

{2-[7-(3-Cyano-pyridin-2-yloxy)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester (119 mg, 0.293 mmol) is dissolved in 10 mL of 1,4 dioxane. The mixture is cooled to zero degrees Celsius in an ice/water bath. To the mixture is added 10 mL of 4N hydrochloric acid in 1,4 dioxane, and the resulting mixture is stirred at zero degrees, under nitrogen, for five hours. The solvent is evaporated, and the residue is taken up in water. The pH of the water is adjusted to 9 using sodium bicarbonate, and is extracted three times with 50 mL of ethyl acetate. The organic layers are combined, dried with sodium sulfate, filtered, and the solvent removed in vacuo to give 218 mg of the title amine (83%). FDMS m/e=307 (M++1).

Workup

  1. temperatureThe mixture is cooled to zero degrees Celsius in an ice/water bath
  2. customThe solvent is evaporated
  3. extractionis extracted three times with 50 mL of ethyl acetate
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a476bb77533b4eeaa2c3f56d95444e50
Source dataset
uspto-grants-2005_06
Patent number
US06911463B2

Reaction notes

Loading…