2-Fluorobenzylamine → 2,2-Diethoxy-N-(2-fluorobenzyl)acetamide

HRID 40686

Reaction equation

HRID 40686 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[CH2:10]([O:12][CH:13]([O:17][CH2:18][CH3:19])[C:14]([O-])=[O:15])[CH3:11].[Na+].O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.C(OCC)(=O)C.O>[CH2:10]([O:12][CH:13]([O:17][CH2:18][CH3:19])[C:14]([NH:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[F:1])=[O:15])[CH3:11]

Participants

9

Reactant 5

HCID 666492-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23663712Sodium diethoxyacetate

Product 1

HCID 596364612,2-Diethoxy-N-(2-fluorobenzyl)acetamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Fluorobenzylamine (2.00 g, 16.0 mmol), sodium 2,2-diethoxyacetate (3.26 g, 19.2 mmol), N-hydroxybenzotriazole hydrate (3.67 g, 24.0 mmol) and diisopropylethylamine (4.18 mL, 24.0 mmol) were stirred in DMF (20 mL) at room temperature. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.6 g, 24.0 mmol) was added and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was diluted water and ethyl acetate. The organic phase was washed sequentially with HCl (aq) (1 M), saturated sodium bicarbonate, water and brine, dried over sodium sulfate and concentrated to dryness. The crude material was used directly in the following reaction.

Workup

  1. washThe organic phase was washed sequentially with HCl (aq) (1 M), saturated sodium bicarbonate, water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness
  4. customThe crude material was used directly in the following reaction

Sources & evidence

ORD record
ord-a3d9951b81a141358391e1e1be6fdcfc
Source dataset
uspto-grants-2013_09
Patent number
US08530468B2

Linked notes

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