Dimethylamine → Octanoic acid, 2-dimethylaminoethyl ester

HRID 1078573Notes

Reaction equation

HRID 1078573 reaction equation
[C:1]([O:10][CH2:11][CH2:12]Br)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:14][NH:15][CH3:16]>C(#N)C>[C:1]([O:10][CH2:11][CH2:12][N:15]([CH3:16])[CH3:14])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 2298832-bromoethyl octanoate

Product 1

HCID 3075918Octanoic acid, 2-dimethylaminoethyl esterYield 83.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bromoethyl octanoate (0.2 g, 0.72 mmol) and 40% aqueous dimethylamine (4.2 mL, 36 mmol) were dissolved in acetonitrile (10 mL). The reaction mixture was stirred at room temperature for 48 hours. After removal of acetonitrile under vacuum, chloroform (30 mL) was added. The chloroform layer was extracted with potassium carbonate solution (20 mL, 0.01N) and water (2×20 mL), then was dried over sodium sulfate. The drying agent was suction filtered, and the chloroform removed in vacuo. The resulting material was applied to a silica gel column (discontinuous gradient of chloroform/methanol 95:5, 8:2 as eluent) affording 0.13 g pure product. Yield 77%; liquid; 1H NMR (CDCl3) 0.85-0.95 (t, CH3 (CH2)4), 1.20-1.40 (m, CH3 (CH2)4), 1.55-1.70 (m, CH2 CH2 CO), 2.25-2.40 (t, CH2 CH2 CO), 2.45-2.55 (s, (CH3)2 N) 2.75-2.85 (t, O CH2 CH2 N), 4.25-4.35 (t, O CH2 CH2 N).

Workup

  1. customAfter removal of acetonitrile under vacuum, chloroform (30 mL)
  2. additionwas added
  3. extractionThe chloroform layer was extracted with potassium carbonate solution (20 mL, 0.01N) and water (2×20 mL)
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered
  6. customthe chloroform removed in vacuo

Sources & evidence

ORD record
ord-4522545b296248d9b6edf4d0601a3aeb
Source dataset
uspto-grants-1996_08
Patent number
US05550132

Reaction notes

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