4-Fluorobenzylamine → HCID 43217378, compound

HRID 2277420Notes

Reaction equation

HRID 2277420 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].[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1.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:19][CH2:18][C:17]1[CH:20]=[CH:21][C:14]([F:13])=[CH:15][CH:16]=1)[CH3:2]

Participants

6

Reactant 3

HCID 673264-FluorobenzylamineHCID 67953Benzoic acid, 2-fluoro-, ethyl esterHCID 81531Diisopropylethylamine

Product 1

HCID 43217378HCID 43217378, 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 4-Fluoro-benzylamine (0.828 g, 6.62 mmol) in dry N,N′-dimethylformamide (10 mL) in a screw cap vial was added diisopropylethylamine (0.854 g, 6.62 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-(4-Fluoro-benzylamino)-benzoic acid ethyl ester as a clear liquid (1.23 g, 75%, LCMS calc M+H 274, obs M+H 274).

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-98f6dbd3072a4600b32bcb94d22835ff
Source dataset
uspto-grants-2015_09
Patent number
US09133164B2

Reaction notes

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