Water → HCID 14772400, compound

HRID 2073712Notes

Reaction equation

HRID 2073712 reaction equation
[N:1]1[O:2][C:3]2[CH2:4][CH2:5][CH2:6][CH:7]3[C:16]=2[C:15]=1[C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:8]3.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][N:8]2[CH:7]3[C:16]4=[C:3]([O:2][N:1]=[C:15]4[C:14]4[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=4)[CH2:4][CH2:5][CH2:6]3)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 135618014HCID 135618014, compound

Product 1

HCID 14772400HCID 14772400, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 40 ml dry DMF were combined 3.00 g 4,5,5a,6-tetrahydro-3H-isoxazolo[5,4,3-kl]acridine, 8.8 ml 4-fluorobenzylbromide and 3 g milled K2CO3. The mixture was stirred mechanically under nitrogen at ambient temperature for 2 days during which the reaction was complete. The reaction mixture was poured into excess water and extracted with DCM. The DCM layer was concentrated to a residue and the residue was triturated with 1:1 methanol/water and recrystallized from 1:1 DCM/hexanes to yield after drying 2.21 g needles, m.p. 214° C. (dec.).

Workup

  1. extractionextracted with DCM
  2. concentrationThe DCM layer was concentrated to a residue
  3. customthe residue was triturated with 1:1 methanol/water
  4. customrecrystallized from 1:1 DCM/hexanes
  5. customto yield
  6. dry with materialafter drying 2.21 g needles, m.p. 214° C. (dec.)

Sources & evidence

ORD record
ord-d1970c037d764a09a4a3d9e3aeff9fcd
Source dataset
uspto-grants-1990_04
Patent number
US04920117

Reaction notes

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