4-Fluorobenzylamine → HCID 18705808, compound

HRID 2287854Notes

Reaction equation

HRID 2287854 reaction equation
[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([C:17]([O-:19])=O)=[C:10]([C:14]([O-])=[O:15])[CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>CC(O)=O>[CH2:20]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:6][C:7]2=[CH:8][C:9]3[C:17](=[O:19])[N:29]([CH2:28][C:27]4[CH:30]=[CH:31][C:24]([F:23])=[CH:25][CH:26]=4)[C:14](=[O:15])[C:10]=3[CH:11]=[C:12]2[CH2:13]1)[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 18705881HCID 18705881, compound

Product 1

HCID 18705808HCID 18705808, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(O'Reilly, N. J., Derwin, W. S., Fertel, L. B., Lin, H. C., Synlett., (1990) 609-610.) A solution of 2-(dipropylamino)-2,3-dihydro-1H-indene-5,6-dicarboxylate (92, 0.35 g, 1.0 mmol) and 4-fluorobenzylamine (0.15 mL, 1.3 mmol) in glacial HOAc (30 mL) was refluxed at 113° C. After 4 h, the reaction was cooled to r.t., concentrated, then azeotroped with toluene. The residue was diluted with water and basified with sat'd Na2CO3 (or sat'd NaHCO3) to pH>12. The solution was extracted with CH2Cl2 and the organic layers were washed with brine, dried (MgSO4), and concentrated. The residue was purified by using silica gel, eluting with 4:1 CH2Cl2/acetone+0.1 % MeOH, to give 101 as a light yellow oil that was converted to an HCl salt and recrystallized from MeOH/EtOAc to give a white solid (m.p. 251-253° C.).

Workup

  1. concentrationconcentrated
  2. customazeotroped with toluene
  3. additionThe residue was diluted with water and basified with sat'd Na2CO3 (or sat'd NaHCO3) to pH>12
  4. extractionThe solution was extracted with CH2Cl2
  5. washthe organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified
  9. washeluting with 4:1 CH2Cl2/acetone+0.1 % MeOH

Sources & evidence

ORD record
ord-fe01c6e9d97344409a9bd360045da101
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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