4-Fluorobenzylamine → HCID 59392856, compound

HRID 222637Notes

Reaction equation

HRID 222637 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]2[C:15]3[C:14]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)=[CH:13][CH:12]=[CH:11][C:10]=3[NH:9][N:8]2[C:22](=[O:25])[C:23]=1[OH:24])=O.C[O-].[Na+].[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=1>CO>[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH:35][C:3]([C:5]2[N:6]=[C:7]3[C:15]4[C:14]([N:16]5[CH2:17][CH2:18][O:19][CH2:20][CH2:21]5)=[CH:13][CH:12]=[CH:11][C:10]=4[NH:9][N:8]3[C:22](=[O:25])[C:23]=2[OH:24])=[O:2])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 673264-FluorobenzylamineHCID 10942334Sodium MethoxideHCID 59392871HCID 59392871, compound

Product 1

HCID 59392856HCID 59392856, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 21.2 (172 mg, 0.5 mmol), sodium methoxide (54 mg, 1.0 mmol) and 4-fluoro benzylamine (1.87 mg, 1.5 mmol) in methanol (15 mL) were combined and heated with stirring at reflux overnight. The mixture was cooled to room temperature and the resulting solid was collected by filtration and dissolved in dichloromethane (30 mL). The solution was washed with aqueous hydrochloric acid (2.0 M), water, dried and concentrated in vacuo to afford desired compound (84 mg, 38.4).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. filtrationthe resulting solid was collected by filtration
  4. dissolutiondissolved in dichloromethane (30 mL)
  5. washThe solution was washed with aqueous hydrochloric acid (2.0 M), water
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0961ea238274de9915ed5c48b35cb44
Source dataset
uspto-grants-2012_06
Patent number
US08207334B2

Reaction notes

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