Oxalate → HCID 66835975, compound

HRID 2404419Notes

Reaction equation

HRID 2404419 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[S:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:21]=1)O.[Na].[C:32]([O-:37])(=[O:36])[C:33]([O-:35])=[O:34]>C1(C)C=CC=CC=1.CC(C)=O.C[C-]1C(C)=C(C)C(C)=C1C.C[C-]1C(C)=C(C)C(C)=C1C.[Cl-].[Cl-].[Cl-].[Cl-].[Ir+3].[Ir+3]>[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[S:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH:18]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1)[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:21]=1

Participants

8

Reactant 4

HCID 71081OxalateHCID 27375314-Amino-1-methylpiperidineHCID 5360545SodiumHCID 66835995HCID 66835995, compound

Product 1

HCID 66835975HCID 66835975, compound

Reagents, catalysts & solvents 3

HCID 7603074312354-84-6CatalystHCID 180AcetoneSolventHCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 4-amino-1-methylpiperidine (0.23 g), benzothiazol-2-yl(3-butoxyphenyl)methanol (0.63 g), sodium hydrogenocarbonate (2 mg) and dichloro(pentamethylcyclopentadienyl)iridium(III) dimer (8 mg) in toluene (3 mL) is heated in an autoclave at 110-120° C. for 66 hours. The mixture is purified by chromatography over silica gel (eluant dichloromethane/methanol:98/2) to give the crude base, which is transformed to the oxalate in acetone to give [benzothiazol-2-yl(3-butoxyphenyl)methyl](1-methylpiperidin-4-yl)amine oxalate melting at 176° C.

Workup

  1. customThe mixture is purified by chromatography over silica gel (eluant dichloromethane/methanol:98/2)
  2. customto give the crude base, which

Sources & evidence

ORD record
ord-0a7fd8a58e03413fa622de8ae4b222d8
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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