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

HRID 2404409Notes

Reaction equation

HRID 2404409 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.[Na].[Ti]>[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 23963TitaniumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 5360545SodiumSolvent

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 tetraisopropoxyde (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), hydrolysed with 3N sodium hydroxyde (30 mL). The organic phase is separated by decantation, washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue is cristallised by trituration in diisopropyl oxyde. A second crop can be obtained form the mother liquor by chromatography over silica gel (gradiant 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. customA second crop can be obtained form the mother liquor by chromatography over silica gel (gradiant dichloromethane/methanol from 98/2 to 95/5)

Sources & evidence

ORD record
ord-428261af7b7e45d39e1d8893c781e5ef
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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