Triethylamine → HCID 22397440, compound

HRID 1060817Notes

Reaction equation

HRID 1060817 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[C:18]([OH:20])=O.Cl.[NH:28]1[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[C:18]([N:28]1[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]1)=[O:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 787643-Methoxy-4-nitrobenzoic acidHCID 30848514-Piperidone hydrochloride

Product 1

HCID 22397440HCID 22397440, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

CDI (9 g) added to a solution of 3-methoxy-4-nitrobenzoic acid (10 g) stirring in THF (200 ml) at RT. After 1 hour, 4-piperidone hydrochloride (6.9 g) and triethylamine (7.8 ml) were added and the mixture stirred overnight. The mixture was diluted with ethyl acetate, washed with 2N HCl (100 ml) then saturated NaHCO3 solution (200 ml) then saturated brine (200 ml). The organic layer was dried (MgSO4) and evaporated to leave a residue which was purified by column chromatography (silica, mixtures of MeOH in dichloromethane) to give the product as a yellow solid (8.5 g; MS: APCI+(M+H) 279).

Workup

  1. washwashed with 2N HCl (100 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customto leave a residue which
  5. customwas purified by column chromatography (silica, mixtures of MeOH in dichloromethane)

Sources & evidence

ORD record
ord-a7632766d10344138c8358ea7b319784
Source dataset
uspto-grants-2003_02
Patent number
US06525070B2

Reaction notes

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