2-(Dimethylamino)ethanol → HCID 58923371, compound

HRID 1951054Notes

Reaction equation

HRID 1951054 reaction equation
[CH2:1]([O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]2[C:14](=[O:31])[C:15]3[C:20]([NH:21][C:22]=2[CH:23]=1)=[CH:19][C:18]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[CH:17][C:16]=3[OH:30])=[O:9])[CH2:2]CCCC.[CH3:32][N:33](C)[CH2:34]CO>CCCCCC>[CH3:32][N:33]([CH3:34])[CH2:2][CH2:1][O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]2[C:14](=[O:31])[C:15]3[C:20]([NH:21][C:22]=2[CH:23]=1)=[CH:19][C:18]([N:24]1[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1)=[CH:17][C:16]=3[OH:30])=[O:9]

Participants

4

Reactant 2

HCID 79022-(Dimethylamino)ethanolHCID 58923368HCID 58923368, compound

Product 1

HCID 58923371HCID 58923371, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

8-Hydroxy-6-morpholin-4-yl-9-oxo-9,10-dihydro-acridine-3-carboxylic acid hexyl ester in. N,N-dimethylethanolamine (2 mL) was heated at 13.0° C. in sealed tube for 12 hours. Hexane (5 mL) was added, and a dark solid formed. The suspension was filtered and the remaining solid triturated with acetone. All residues were dissolved in MeOH and concentrated. The concentrate was purified via flash chromatography (CH2Cl2 to MeOH/CH2Cl2, 5:95) to yield an orange solid (10 mg, 27%). 1H NMR (CDCl3, 400 MHz) δ: 13.82 (s, 1H), 11.84 (s, 1H), 8.19 (d, 1H), 8.04 (s, 1H), 7.66 (d, 1H), 6.24 (s, 1H), 6.16 (s, 1H), 4.41 (t, 2H), 3.74-3.64 (m, 4H), 3.33-3.22 (m, 4H), 2.64 (t, 2H), 2.48 (s, 6H) LRMS (APCI, positive): Da/e 412.1 (m+1).

Workup

  1. customa dark solid formed
  2. filtrationThe suspension was filtered
  3. customthe remaining solid triturated with acetone
  4. dissolutionAll residues were dissolved in MeOH
  5. concentrationconcentrated
  6. customThe concentrate was purified via flash chromatography (CH2Cl2 to MeOH/CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-0f9e0215e24e447ab4013a01b55916b4
Source dataset
uspto-grants-2013_03
Patent number
US08404681B2

Reaction notes

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