Hydrochloric Acid → 2-(Morpholin-4-yl)acetic acid hydrochloride

HRID 61299Notes

Reaction equation

HRID 61299 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([O:10]C(C)(C)C)=[O:9])[CH2:3][CH2:2]1.[ClH:15]>O1CCOCC1.C(OCC)C>[ClH:15].[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 104428104-Morpholineacetic acid, 1,1-dimethylethyl ester

Product 1

HCID 177509462-(Morpholin-4-yl)acetic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl 2-morpholinoacetate (11 g, 54.7 mmol) was stirred with HCl, 4M in dioxane (54 mL), giving a white precipitate (a mild exotherm was observed) which slowly dissolved with stirring at room temperature. Ten minutes after complete dissolution, the mixture solidified. Then the mixture was warmed to 60° C. and the thick suspension was stirred vigorously overnight. The mixture was then cooled to room temperature, diluted with diethyl ether (60 mL) and filtered to collect the title compound (8 g, 80%) as a white solid. 1H NMR (CD3OD, 400 MHz): δ (ppm) 4.13 (s, 2H), 3.94 (brm, 4H), 3.41 (brm, 4H).

Workup

  1. customgiving a white precipitate (a mild exotherm
  2. dissolutionslowly dissolved
  3. dissolutionTen minutes after complete dissolution
  4. temperatureThen the mixture was warmed to 60° C.
  5. stirringthe thick suspension was stirred vigorously overnight
  6. temperatureThe mixture was then cooled to room temperature
  7. filtrationfiltered
  8. customto collect the title compound (8 g, 80%) as a white solid

Sources & evidence

ORD record
ord-39f24acd253746de84cead7c8fabe78f
Source dataset
uspto-grants-2016_09
Patent number
US09441012B2

Reaction notes

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