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Propanolamine ethyl ether → N-Anthracen-9-ylmethyl-N'-(3-ethoxy-propyl)-N-ethyl-propane-1,3-diamine

HRID 12996
Notes
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Reaction equation

HRID 12996 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][N:16]([CH2:25][CH3:26])[CH2:17][CH2:18][CH2:19]OS(C)(=O)=O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[CH2:27]([O:29][CH2:30][CH2:31][CH2:32][NH2:33])[CH3:28]>C(#N)C>[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[CH2:15][N:16]([CH2:25][CH3:26])[CH2:17][CH2:18][CH2:19][NH:33][CH2:32][CH2:31][CH2:30][O:29][CH2:27][CH3:28])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 22720Propanolamine ethyl etherHCID 86615041Methanesulfonic acid 3-(anthracen-9-ylmethyl-ethyl-amino)-propyl ester

Product 1

HCID 24744196N-Anthracen-9-ylmethyl-N'-(3-ethoxy-propyl)-N-ethyl-propane-1,3-diamineYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

The mesylate 17 (584 mg, 1.57 mmol) and 3-ethoxypropylamine (649 mg, 6.30 mmol) were dissolved in acetonitrile (30 mL). The mixture was then stirred at 75° C. under a N2 atmosphere overnight. After the confirmation of the disappearance of the mesylate by TLC, the solution was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (25 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 19 as a light yellow oil. Yield 60%; Rf=0.35 (0.5:4:85.5 NH4OH:MeOH:CH2Cl2); 1H NMR (CDCl3) δ 8.43 (d, 2H), 8.29 (s, 1H), 7.89 (d, 2H), 7.40 (m, 4H), 4.38 (s, 2H), 3.35 (q, 2H), 3.25 (t, 2H), 2.62 (q, 2H), 2.44 (t, 2H), 2.27 (t, 2H), 2.23 (t, 2H), 1.54 (q, 2H), 1.41 (q, 2H), 1.14 (m, 6H); 13C NMR (CDCl3) δ 131.3, 131.2, 130.6, 128.9, 127.2, 125.4, 125.0, 124.7, 69.1, 66.0, 50.7, 50.6, 48.2, 47.5, 47.2, 30.1, 27.1, 15.4, 11.9.

Workup

  1. concentrationAfter the confirmation of the disappearance of the mesylate by TLC, the solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2 (25 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-90a9e413fceb40e598299cf0c7f7ac3f
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728041B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes