4-Amino-1-methylpiperidine → HCID 86695318, compound

HRID 572821Notes

Reaction equation

HRID 572821 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=1)=O.[NH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1>O1CCCC1.C(OCC)(=O)C.[OH-].[Na+].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10](=[N:19][CH:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1)[C:12]1[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 2

HCID 27375314-Amino-1-methylpiperidineHCID 66836093HCID 66836093, compound

Product 1

HCID 86695318HCID 86695318, compound

Reagents, catalysts & solvents 4

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

Procedure

To a solution of (benzothiazol-2-yl)(m-tolyl)methanone (1.06 g) and 4-amino-1-methylpiperidine (0.456 g) in tetrahydrofurane (4 mL) is added titanium tetraisopropoxide (1.42 g). The mixture is stirred at room temperature for 1 h, then polymethyl hydrosiloxane (1.2 mL) is added. The mixture is stirred for one day at room temperature, diluted with ethyl acetate (50 mL), hydolysed with 3N sodium hydroxide (30 mL). The organic phase is separated by decantation, washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue is crystallised by trituration in diisopropyl oxide. A second crop can be obtained form the mother liquor by chromatography over silica gel (gradient dichloromethane/methanol from 98/2 to 95/5) to give [(benzothiazol-2-yl)(m-tolyl)methylene](1-methylpiperidin-4-yl)amine meting at 125° C.

Workup

  1. stirringThe mixture is stirred for one day at room temperature
  2. customThe organic phase is separated by decantation
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is crystallised by trituration in diisopropyl oxide
  7. customA second crop can be obtained form the mother liquor by chromatography over silica gel (gradient dichloromethane/methanol from 98/2 to 95/5)

Sources & evidence

ORD record
ord-329e5c0a15bb46979a0d59bb8e4945e4
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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