Morpholine → 4-(2-(1H-Indol-3-yl)ethyl)morpholine

HRID 1095534

Reaction equation

HRID 1095534 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1>O1CCOCC1>[NH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH2:9][CH2:8][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:11]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 769243-(2-Bromoethyl)indole

Product 1

HCID 2135274-(2-(1H-Indol-3-yl)ethyl)morpholine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Morpholine (2.33 g, 2.33 ml, 26.8 mmol) was dissolved in abs. dioxane (50 ml), and 3-(2-bromo-ethyl)-1H-indole (3.00 g, 13.4 mmol) was added at RT. The solution was stirred at 70° C. for 14 h and concentrated i. vac., the residue was taken up in CHCl3 (100 ml) and the mixture was washed with water (2×30 ml). The organic phase was dried over Na2SO4, filtered and concentrated i. vac. The residue obtained was recrystallized from aqueous methanol.

Workup

  1. concentrationconcentrated i
  2. washthe mixture was washed with water (2×30 ml)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated i
  6. customThe residue obtained
  7. customwas recrystallized from aqueous methanol

Sources & evidence

ORD record
ord-4845a4d355434365aab47625494f14fb
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Linked notes

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