Dicyclohexylcarbodiimide → HCID 15378692, compound

HRID 2211558Notes

Reaction equation

HRID 2211558 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.[CH3:20][C:21]1[CH:22]=[C:23]2[C:28](=O)[O:27][C:25](=[O:26])[C:24]2=[CH:30][CH:31]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[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:28](=[O:27])[C:23]5=[CH:22][C:21]([CH3:20])=[CH:31][CH:30]=[C:24]5[C:25]4=[O:26])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 880694-Methylphthalic anhydrideHCID 146998572-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethan-1-amine

Product 1

HCID 15378692HCID 15378692, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.44 gm, 9.24 mmoles), 4methylphthalic anhydride (1.76 gm, 10.8 mmoles) and dicyclohexylcarbodiimide (2 gm, 1,0 mmoles) in dichloromethane (DCM 100 ml) was stirred at room temperature for 2 hr. The insolubles were filtered off. The DCM solution was concentrated to a crude solid. This was purified on at flash chromatography column (35 gm, SiO3, Sorbsil-C-30; eluted with 1% CH3OH in 99% DCM). The material thus purified weighed 1.0 gm (26%) as a white solid. Recrystallization from hot ethanol gave 665 mg of crystals, m.p.=138°-140°]C.

Workup

  1. filtrationThe insolubles were filtered off
  2. concentrationThe DCM solution was concentrated to a crude solid
  3. customThis was purified on at flash chromatography column (35 gm, SiO3
  4. washeluted with 1% CH3OH in 99% DCM)
  5. customThe material thus purified
  6. customRecrystallization from hot ethanol

Sources & evidence

ORD record
ord-7df05d4355ae405185ece84ee514f666
Source dataset
uspto-grants-2006_09
Patent number
USRE039265E1

Reaction notes

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