1-Hydroxybenzotriazole → 10,11-DIHYDRO-5-[1-(1-(4-PYRIDYL)METHYLCARBONYL)-4-PIPERIDYLIDENE]-5H-DIBENZO[a,d]CYCLOHEPTENE

HRID 840270Notes

Reaction equation

HRID 840270 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=[C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][CH2:10][C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]2=3)[CH2:3][CH2:2]1.Cl.[N:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=1.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[N:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([N:1]2[CH2:2][CH2:3][C:4](=[C:7]3[C:8]4[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=4[CH2:10][CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]3=4)[CH2:5][CH2:6]2)=[O:31])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 810974-Pyridineacetic acid hydrochlorideHCID 1201458Desloratadine impurity 24

Product 1

HCID 2262192010,11-DIHYDRO-5-[1-(1-(4-PYRIDYL)METHYLCARBONYL)-4-PIPERIDYLIDENE]-5H-DIBENZO[a,d]CYCLOHEPTENE

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 0.15 g (0.6 m mole) of 10,11-dihydro-5-(4-piperidylidene)-5H-dibenzo[a,d]cycloheptene, 0.096 g (0.55 m mole) of 4-pyridylacetic acid hydrochloride, 0.16 g (0.83 m mole) of DEC and 0.075 g (0.55 m mole) of HOBT in 5 mL of DMF and stir at room temperature for 18 hours under nitrogen. Concentrate under vacuo and partition between 100 mL each of EtOAc and 10% aqueous sodium hydrogenphosphate. Dry the organic layer over MgSO4 and concentrate under vacuo. The resulting residue is chromatographed on silica gel using 98% dichloro methane and 2% MeOH, saturated with ammonia as the solvent, giving the product as a white waxy solid, mp=162.8-163.4° C.

Workup

  1. concentrationConcentrate under vacuo
  2. custompartition between 100 mL each of EtOAc and 10% aqueous sodium hydrogenphosphate
  3. dry with materialDry the organic layer over MgSO4
  4. concentrationconcentrate under vacuo
  5. customThe resulting residue is chromatographed on silica gel using 98% dichloro methane and 2% MeOH, saturated with ammonia as the solvent
  6. customgiving the product as a white waxy solid, mp=162.8-163.4° C.

Sources & evidence

ORD record
ord-337060c864b64ca1ac1529eb49aac9a2
Source dataset
uspto-grants-2002_04
Patent number
US06365588B1

Reaction notes

Loading…