Triethylamine → HCID 18467274, compound

HRID 370254Notes

Reaction equation

HRID 370254 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.C(N(CC)CC)C.[ClH:27].[C:28]([Cl:36])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=1>C(Cl)(Cl)Cl.C(Cl)Cl>[OH2:8].[ClH:36].[ClH:27].[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][NH:17][C:28]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)=[O:35])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 146998572-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethan-1-amine

Product 1

HCID 18467274HCID 18467274, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (1.17 g, 4.34 mmol) and triethylamine (1.08 g, 10.8 mmol) in chloroform (30 ml) was added nicotinoyl chloride hydrochloride (0.96 g, 5.4 mmol) in one portion. The mixture was stirred for 1 hour at room temperature. The solution was diluted with methylene chloride (DCM) and washed with brine and dried over anhydrous MgSO4. The solution was concentrated and the crude product was purified by flash chromatography over a silica gel column (SiO2, 25 g; eluted with DCM and 1-3% MeOH in DCM). The free base thus purified weighed 1.7 g. This product was treated with 1M· HCl in ethanol and recrystallized twice from methanol:isiproply ether to yield white crystals, 1.19 g, m.p. 243-245° C. as a dihydrochloride hydrate.

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationThe solution was concentrated
  4. customthe crude product was purified by flash chromatography over a silica gel column (SiO2, 25 g; eluted with DCM and 1-3% MeOH in DCM)
  5. customThe free base thus purified
  6. additionThis product was treated with 1M· HCl in ethanol
  7. customrecrystallized twice from methanol

Sources & evidence

ORD record
ord-2bf89eb92ad34b699414fed419176da1
Source dataset
uspto-grants-2000_10
Patent number
US06140345

Reaction notes

Loading…