Dicyclohexylcarbodiimide → HCID 15340829, compound

HRID 2257686Notes

Reaction equation

HRID 2257686 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.[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:23]([C:24](O)=[O:25])[C:22]=1[C:30](O)=[O:31].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:30](=[O:31])[C:22]5=[C:21]([F:20])[CH:29]=[CH:28][CH:27]=[C:23]5[C:24]4=[O:25])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 3453813-Fluorophthalic acidHCID 146998572-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethan-1-amine

Product 1

HCID 15340829HCID 15340829, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.37 gm, 8.98 mmoles), 3-fluorophthalic acid (1.82 gm, 9.9 moles) and dicyclohexylcarbodiimide (DCC, 5.5 gm, 26.7 mmoles, 2.6 eq) in dichloromethane (DCM, 250 ml) was stirred at room temperature for 18 hrs. The solids were filtered off. The organic solution was concentrated down. The residue was purified on a flash chromatography column (SiO2, 50 gm; eluted with 1% CH3OH:99% DCM, 1.4 liter; 2-6% CH3OH:DCM, 1 liter). The desired product thus obtained weighed 2.64 gm (71%) as an off-white solid. Recrystallization from hot ethanol gave 1.41 gm of white crystals, m.p.=142°-143° C.

Workup

  1. filtrationThe solids were filtered off
  2. concentrationThe organic solution was concentrated down
  3. customThe residue was purified on a flash chromatography column (SiO2, 50 gm; eluted with 1% CH3OH:99% DCM, 1.4 liter; 2-6% CH3OH:DCM, 1 liter)

Sources & evidence

ORD record
ord-804d6c2878b84aed8d6b914b4e7df89a
Source dataset
uspto-grants-1997_08
Patent number
US05658911

Reaction notes

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