Hydrochloric Acid → HCID 23508187, compound

HRID 1883602Notes

Reaction equation

HRID 1883602 reaction equation
C([SiH2][O:6][C:7](C)(C)[CH:8]([NH:18]C(=O)C)[CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[O:16][CH3:17])(C)(C)C.Cl.[OH-].[Na+]>>[NH2:18][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[O:16][CH3:17])[CH2:7][OH:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131724498HCID 131724498, compound

Product 1

HCID 23508187HCID 23508187, compoundYield 46.4%

Conditions

Temperature
100 °C

Procedure

A mixture of 1.2 g of N-[1-(tert-butyl-dimethyl-silanyloxymethyl)-2-(3-methoxy-pyridin-4-yl)ethyl]-acetamide in 60 mL of aqueous solution of 6N hydrochloric acid is heated at a temperature of about 100° C. for 30 minutes. After cooling at a temperature of about 20° C., an adequate volume of an aqueous 30% sodium hydroxide solution is added dropwise to obtain a pH of about 10. The mixture is extracted with 3 times 100 mL of ethyl acetate and the organic extracts are combined, dried over magnesium sulfate then concentrated under reduced pressure (2 kPa) at a temperature of about 40° C. About 0.3 g of 2-amino-3-(3-methoxy-pyridin-4-yl)-1-propanol is obtained in the form of an yellow-colored oil. [Infrared spectrum CH2Cl2: 3628; 3335; 2948; 1614; 1561; 1400; 1319; 1162; 1044 et 815 cm−1].

Workup

  1. temperatureAfter cooling at a temperature of about 20° C.
  2. customto obtain a pH of about 10
  3. extractionThe mixture is extracted with 3 times 100 mL of ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationthen concentrated under reduced pressure (2 kPa) at a temperature of about 40° C

Sources & evidence

ORD record
ord-33a29e8fa49f4fdb884e7748b754a223
Source dataset
uspto-grants-2004_07
Patent number
US06762196B2

Reaction notes

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