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

HRID 2404411Notes

Reaction equation

HRID 2404411 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.[Na].[Ti]>[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 23963TitaniumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 5360545SodiumSolvent

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 tetraisopropoxyde (1.78 g). The suspension is stirred for 24 h at room temperature, diluted with ethyl acetate and 1N sodium hydroxyde. 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 (gradiant 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 (gradiant dichloromethane/methanol from 100/0 to 90/10)

Sources & evidence

ORD record
ord-ba1dc605238e485c872be5f7521146d5
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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