Ethoxyethylamine → HCID 70873910, compound

HRID 2277429Notes

Reaction equation

HRID 2277429 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1F)[CH3:2].[CH2:13]([O:15][CH2:16][CH2:17][NH2:18])[CH3:14].C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:18][CH2:17][CH2:16][O:15][CH2:13][CH3:14])[CH3:2]

Participants

6

Reactant 3

HCID 66970EthoxyethylamineHCID 67953Benzoic acid, 2-fluoro-, ethyl esterHCID 81531Diisopropylethylamine

Product 1

HCID 70873910HCID 70873910, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of commercially available 2-Fluoro-benzoic acid ethyl ester (1 g, 6.01 mmol) and 2-Ethoxy-ethylamine (0.500 g, 2.97 mmole) in dry N,N′dimethylformamide (10 mL) in a screw cap vial was added diisopropylethylamine (1.1 eq, 0.223 g, 3.27 mmole, 1.1 mL). The resulting solution was heated to 120° C. for 4 hours. Reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate (25 mL×3). Combined organic phase was washed consecutively with water, brine before drying over sodium sulfate. Organic phase was evaporated and the residue was purified by flash chromatography to afford 2-(2-Ethoxy-ethylamino)-benzoic acid ethyl ester as a clear liquid (0.493 g, 70%, LCMS calc M+H 238, obs M+H 238).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. extractionextracted with ethyl acetate (25 mL×3)
  4. washCombined organic phase was washed consecutively with water, brine
  5. dry with materialbefore drying over sodium sulfate
  6. customOrganic phase was evaporated
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-91d6690ea3bc4e67b839d863a8e3c368
Source dataset
uspto-grants-2015_09
Patent number
US09133164B2

Reaction notes

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