Triethylamine → HCID 68536996, compound

HRID 1993667Notes

Reaction equation

HRID 1993667 reaction equation
C(N(CC)CC)C.Cl.Cl.[N+:10]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([O:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:14]=1)([O-:12])=[O:11].[F:26][C:27]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:28]=1[C:29](Cl)=[O:30]>ClCCl>[F:26][C:27]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:28]=1[C:29]([N:23]1[CH2:24][CH2:25][CH:20]([O:19][C:15]2[CH:14]=[C:13]([N+:10]([O-:12])=[O:11])[CH:18]=[CH:17][N:16]=2)[CH2:21][CH2:22]1)=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 68538445HCID 68538445, compound

Product 1

HCID 68536996HCID 68536996, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add triethylamine (2.57 mL, 18.5 mmol) to a suspension of 1.1 g (3.7 mmol) of 4-nitro-2-(piperidin-4-yloxy)-pyridine dihydrochloride in dry dichloromethane (50 mL). Then add 2,6-difluorobenzoyl chloride, 0.512 mL (4.07 mmol). Stir the mixture at room temperature overnight. Add water (50 mL) and separate organic layer. Dry with MgSO4 and filter. Evaporate solvents to obtain 1.22 g (91% yield) of (2,6-difluoro-phenyl)-[4-(4-nitro-pyridin-2-yloxy)-piperidin-1-yl]-methanone as a yellow solid (ES+(m/z)=364 [M+H].

Workup

  1. customAdd water (50 mL) and separate organic layer
  2. dry with materialDry with MgSO4
  3. filtrationfilter

Sources & evidence

ORD record
ord-37396d23fd6d4733bf4e7855bdbd753b
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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