4-Amino-1-methylpiperidine → HCID 86695319, compound

HRID 572822Notes

Reaction equation

HRID 572822 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1)=O.[NH2:21][CH:22]1[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]1>O1CCCC1.C(OCC)(=O)C.[OH-].[Na+].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10](=[N:21][CH:22]1[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]1)[C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1

Participants

7

Reactant 2

HCID 27375314-Amino-1-methylpiperidineHCID 66836028HCID 66836028, compound

Product 1

HCID 86695319HCID 86695319, compound

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of (benzofuran-2-yl)(benzothiazol-2-yl)methanone (1.4 g) and 4-amino-1-methylpiperidine (0.57 g) in tetrahydrofurane (8 mL) is added dropwise titanium tetraisopropoxide (1.78 g). The suspension is stirred for 24 h at room temperature, diluted with ethyl acetate and 1N sodium hydroxide. The precipitate is filtered over a clarcel pad and rinsed with ethyl acetate. The pooled filtrates are washed with saturated sodium chloride solution, dried and concentrated under reduced pressure. The residue is purified over silica gel (gradient dichloromethane/methanol from 100/0 to 90/10) to afford [(benzofuran-2-yl)(benzothiazol-2-yl)methylene](1-methylpiperidin-4-yl)amine.

Workup

  1. filtrationThe precipitate is filtered over a clarcel pad
  2. washrinsed with ethyl acetate
  3. washThe pooled filtrates are washed with saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified over silica gel (gradient dichloromethane/methanol from 100/0 to 90/10)

Sources & evidence

ORD record
ord-147a487d94894c7da5204031d6224517
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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