4,5-Dichlorophthalic anhydride → HCID 15380105, compound

HRID 2257682Notes

Reaction equation

HRID 2257682 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH2:17])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[Cl:20][C:21]1[CH:22]=[C:23]2[C:28](=O)[O:27][C:25](=[O:26])[C:24]2=[CH:30][C:31]=1[Cl:32]>C(Cl)Cl>[F:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]4[C:25](=[O:26])[C:24]5=[CH:30][C:31]([Cl:32])=[C:21]([Cl:20])[CH:22]=[C:23]5[C:28]4=[O:27])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 703344,5-Dichlorophthalic anhydrideHCID 146998572-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethan-1-amine

Product 1

HCID 15380105HCID 15380105, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.83 gm, 10.7 mmol) and 4,5-dichlorophthalic anhydride (2.56 gm, 11.93 mmol, 1.1 eq) in methylene chloride (100 ml, DCM) was stirred for 2 h, white solids precipitated and the TLC showed disappearance of the starting material. The solvent was removed, and the crude solid was loaded onto a flash chromatography column (28 gm, SiO2, sorbsil C-30, eluted with 1% MeOH in DCM; 0.5% of NH4OH was added towards the end of elution). The material thus purified weighed 2.26 gm as white crystals. Recrystallization twice from a large volume of hot ethanol (400 ml) yielded 1.57 gm of white shining crystals, m.p.=132°-134° C.

Workup

  1. customwhite solids precipitated
  2. customThe solvent was removed
  3. washeluted with 1% MeOH in DCM
  4. addition0.5% of NH4OH was added towards the end of elution)
  5. customThe material thus purified
  6. customRecrystallization twice from a large volume of hot ethanol (400 ml)
  7. customyielded 1.57 gm

Sources & evidence

ORD record
ord-786c4731b66b4b74b09fb8cc9f2c0c62
Source dataset
uspto-grants-1997_08
Patent number
US05658911

Reaction notes

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