Gamma-Butyrolactone → HCID 178516224, compound

HRID 1173816Notes

Reaction equation

HRID 1173816 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.[C:9]1(=O)[O:13][CH2:12][CH2:11][CH2:10]1>O>[OH:8][C@H:5]1[CH2:6][CH2:7][C@H:2]([N:1]2[CH2:9][CH2:10][CH2:11][C:12]2=[O:13])[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 7302Gamma-ButyrolactoneHCID 178511715HCID 178511715, compound

Product 1

HCID 178516224HCID 178516224, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

Add trans-4-aminocyclohexanol (230 g; 2.0 mol) to γ-butyrolactone (140 mL; 1.82 mol) in a 1 L round-bottom flask equipped with large magnetic stirrer, thermometer and condenser/nitrogen bubbler. Heat at 190° C. for 68 hours. Cool to ambient temperature and dissolve in water (1 L). Extract into dichloromethane (10×1.5 L). Dry the extracts over magnesium sulfate, filter and evaporate to a brown solid. Triturate with diethyl ether to afford 144.7 g (43%) of the title compound: LC-MS (M+1=184).

Workup

  1. customequipped with large magnetic stirrer
  2. temperatureCool to ambient temperature
  3. extractionExtract into dichloromethane (10×1.5 L)
  4. dry with materialDry the extracts over magnesium sulfate
  5. filtrationfilter
  6. customevaporate to a brown solid
  7. customTriturate with diethyl ether

Sources & evidence

ORD record
ord-d2036d99a6a94920b0759c847f0baef6
Source dataset
uspto-grants-2010_11
Patent number
US07834194B2

Reaction notes

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