Morpholine → HCID 57178693, compound

HRID 1047652Notes

Reaction equation

HRID 1047652 reaction equation
CC(C)([O-])C.[Na+].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[Br:13][CH:14](Br)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>C1COCC1>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 118068541,1-DibromohexaneHCID 23676156Sodium t-butoxide

Product 1

HCID 57178693HCID 57178693, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

Under nitrogen 250 ml anhydrous THF were added to 37 g (1.1 eq, 385 mmol) sodium tert-butoxide. Then 30.45 g (1 eq, 350 mmol) morpholine were added neat. The suspension was heated to 50° C. for 1 h. After cooling to RT, 1.21 anhydrous THF and 85.29 g (1 eq, 350 mmol) dibromohexane in ˜150 ml anhydrous THF were added. After 1 h at RT the mixture was heated to 85° C. over night. The overstanding solution was decanted and all volatiles removed in vacuo. The residue was dissolved in ether and water and the organic layer extracted with 2M hydrochloric acid. After dilution with water and ether, KOH flakes were added under vigorous stirring and cooling until pH=10. After phase separation, the aqueous layer was extracted with ether. The combined organic layers were dried over brine and MgSO4 and all volatiles removed to yield 40 g. Further purification by column chromatography (70% hexane, 30% ethyl acetate, 5% triethylamine) yielded 14.56 g, 99% by GCMS. 1H-NMR (400 MHz, CDCl3): [ppm]=3.71 (t, J=4 Hz, 4H), 3.41 (t, J=6.8 Hz, 2H), 2.42 (t, J=4 Hz, 4H), 2.32 (t, J=7.6 Hz, 2H), 1.48 (m, 4H), 1.34 (m, 2H).

Workup

  1. temperatureAfter cooling to RT
  2. temperatureAfter 1 h at RT the mixture was heated to 85° C. over night
  3. customThe overstanding solution was decanted
  4. customall volatiles removed in vacuo
  5. dissolutionThe residue was dissolved in ether
  6. extractionwater and the organic layer extracted with 2M hydrochloric acid
  7. additionAfter dilution with water and ether, KOH flakes were added
  8. temperaturecooling until pH=10
  9. customAfter phase separation
  10. extractionthe aqueous layer was extracted with ether
  11. dry with materialThe combined organic layers were dried over brine and MgSO4
  12. customall volatiles removed
  13. customto yield 40 g
  14. customFurther purification by column chromatography (70% hexane, 30% ethyl acetate, 5% triethylamine)
  15. customyielded 14.56 g, 99% by GCMS

Sources & evidence

ORD record
ord-5dd45743f5d24c0286b307a962347477
Source dataset
uspto-grants-2013_10
Patent number
US08569752B2

Reaction notes

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