2,6-Pyridinedicarboxylic acid → HCID 18348594, compound

HRID 2268530Notes

Reaction equation

HRID 2268530 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]2[CH2:30][C:29]3[C:24](=[C:25]([O:37]C)[C:26]([O:35][CH3:36])=[C:27]([O:33][CH3:34])[C:28]=3[O:31]C)[CH2:23]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(C(O)=O)=CC=CC=1C(O)=O.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C(=O)(O)[O-].[Na+]>O.C1COCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]2[CH2:30][C:29]3[C:28](=[O:31])[C:27]([O:33][CH3:34])=[C:26]([O:35][CH3:36])[C:25](=[O:37])[C:24]=3[CH2:23]2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 18348577HCID 18348577, compound

Product 1

HCID 18348594HCID 18348594, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-benzyl-1-[8-(4,5,6,7-tetramethoxyindan-2-yl)octyl]piperazine (676 mg), 2,6-pyridinedicarboxylic acid (647 mg), THF (14 ml), and water (7 ml) was dropwise added a solution of CAN (2.83 g) in water (7 ml) with cooling with ice. After the reaction mixture was stirred for 15 min, saturated aqueous sodium bicarbonate was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was recrystallized from hexane-ethyl acetate to yield the entitled compound (380 mg) as crystals.

Workup

  1. temperaturewith cooling with ice
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-c17d99eb645a456b898e4cec8c6b8e54
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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