Hydrochloric Acid → Dodecylamine

HRID 1272220Notes

Reaction equation

HRID 1272220 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-cd3716a8dafd487fb0f3540e52bd1d64
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Reaction notes

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