4-Fluorobenzylamine → HCID 21961384, compound

HRID 2211676Notes

Reaction equation

HRID 2211676 reaction equation
F[C:2]1[N:26]=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:22])([CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH3:14])=[CH:9][CH:8]=1)=[O:5].[F:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[F:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH:33][C:2]2[N:26]=[CH:25][CH:24]=[CH:23][C:3]=2[C:4]([NH:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]([CH3:22])([CH:15]3[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]3)[CH3:14])=[CH:9][CH:8]=2)=[O:5])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 673264-FluorobenzylamineHCID 516892Sodium BicarbonateHCID 21959663HCID 21959663, compound

Product 1

HCID 21961384HCID 21961384, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
105 °C

Procedure

A solution of 2-fluoro-N-{4-[1-methyl-1-(1-methyl-piperidin-4-yl)-ethyl]-phenyl}-nicotinamide (355 mg) and 4-fluorobenzylamine (250 mg) in pyridine (10 mL) was suspended with NaHCO3 (1 g). The mixture was heated to 105° C. overnight. Solids were removed by filtration and the filtrate was concentrated in vacuo. The residue was purified on prep. TLC plates (silica, EtOAc:TEA=10:1) to provide the desired product. MS (ES+): 461 (M+1)+, Calc'd for C28H33FN4O-460.59.

Workup

  1. customSolids were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified on prep

Sources & evidence

ORD record
ord-6b8f560536db4002aa01c33d70d7e353
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

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