Ethyl Bromide → 3-(Anthracen-9-ylmethyl-ethyl-amino)-propan-1-OL

HRID 13003

Reaction equation

HRID 13003 reaction equation
Br[CH2:2][CH3:3].[CH:4]1[C:17]2[C:8](=[CH:9][C:10]3[C:15]([C:16]=2[CH2:18][NH:19][CH2:20][CH2:21][CH2:22][OH:23])=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:7]=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH:14]1[C:15]2[C:10](=[CH:9][C:8]3[C:17]([C:16]=2[CH2:18][N:19]([CH2:2][CH3:3])[CH2:20][CH2:21][CH2:22][OH:23])=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 114710953-[(Anthracen-9-ylmethyl)-amino]-propan-1-OL

Product 1

HCID 116879303-(Anthracen-9-ylmethyl-ethyl-amino)-propan-1-OLYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

Bromoethane (616 mg, 5.65 mmol) was dissolved in anhydrous acetonitrile and was added to the stirring mixture of compound 14a (500 mg, 1.9 mmol) and anhydrous K2CO3 (781 mg, 5.7 mmol). The mixture was then stirred overnight at 75° C. under a N2 atmosphere. After confirmation of the disappearance of 14a by TLC, the solution was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (20 mL) and washed three times with aqueous sodium carbonate. The organic layer was separated, dried with anhydrous Na2SO4, filtered and concentrated under vacuum. Flash column chromatography of the residue gave 14b as a light yellow oil. Yield 82%; Rf=0.35 (3% MeOH/CHCl3); 1H NMR (CDCl3) δ 8.28 (m, 3H), 7.86 (d, 2H), 7.44 (m, 2H), 7.36 (m, 2H), 4.29 (s, 2H), 3.15 (t, 2H), 2.65 (q, 2H), 2.52 (t, 2H), 1.43 (q, 2H), 1.16 (t, 3H); 13C NMR (CDCl3) δ 131.2, 131.1, 129.3, 129.0, 127.6, 125.8, 124.8, 124.4, 63.4, 52.6, 50.5, 47.7, 28.1, 11.6. HRMS (FAB) m/z calcd. for C20H23NO (M+H)+ 294.1852; found 294.1859.

Workup

  1. concentrationAfter confirmation of the disappearance of 14a by TLC, the solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  3. washwashed three times with aqueous sodium carbonate
  4. customThe organic layer was separated
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-13cde27d90644357aafc71add8c12392
Source dataset
uspto-grants-2010_06
Patent number
US07728041B2

Linked notes

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