2,6-Pyridinedicarboxylic acid → HCID 18348592, compound

HRID 2268537Notes

Reaction equation

HRID 2268537 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][C:22]2([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[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][C:22]2([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:23][C:24]3[C:25](=[O:37])[C:26]([O:35][CH3:36])=[C:27]([O:33][CH3:34])[C:28](=[O:31])[C:29]=3[CH2:30]2)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 18348561HCID 18348561, compound

Product 1

HCID 18348592HCID 18348592, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-benzyl-1-[8-(4,5,6,7-tetramethoxy-2-phenylindan-2-yl)octyl]piperazine (713 mg), 2,6-pyridinedicarboxylic acid (597 mg), THF (14 ml), and water (7 ml) was dropwise added a solution of CAN (2.59 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 and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by alumina column chromatography (hexane to hexane:ethyl acetate 8:1) and then with recrystallization from hexane-diethyl ether to yield the entitled compound (310 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 and saturated aqueous sodium chloride
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by alumina column chromatography (hexane to hexane:ethyl acetate 8:1)
  7. customwith recrystallization from hexane-diethyl ether

Sources & evidence

ORD record
ord-326e4053192c4377bee7d922750e1dfd
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

Loading…