Trityl chloride → HCID 71246274, compound

HRID 1486811Notes

Reaction equation

HRID 1486811 reaction equation
[CH:1]12[NH:17][CH:5]([CH:6]([C:8]3[CH:9]=[CH:10][C:11]([N:14]([CH3:16])[CH3:15])=[N:12][CH:13]=3)[CH2:7]1)[CH2:4][CH2:3][CH2:2]2.[C:18](Cl)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[CH3:16][N:14]([CH3:15])[C:11]1[CH:10]=[CH:9][C:8]([CH:6]2[CH2:7][CH:1]3[N:17]([C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:5]2[CH2:4][CH2:3][CH2:2]3)=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 6456Trityl chloride2×HCID 71246677HCID 71246677, compound

Product 1

HCID 71246274HCID 71246274, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

217 mg (0.94 mmol, 1 eq) of (−)-[5-(8-aza-bicyclo[3.2.1]oct-6-yl)-pyridine-2-yl]-dimethylamine (VII-1) are dissolved in 1 ml of chloroform. 195 μL (1.4 mmol, 1.5 eq) of TEA and 274 mg (0.98 mmol, 1.05 eq) of tritylchloride are added. After stirring for 1 and 2.5 h at RT 195 μL (1.4 mmol, 1.5 eq) of TEA and 274 mg (0.98 mmol, 1.05 eq) of tritylchloride are added. After stirring for a total of 4 h at RT it is diluted with EE. It is washed once with water, the aqueous phase is re-extracted twice with EE. The combined organic phases are dried over sodium sulphate and the solvent is removed in vacuo. The crude product is purified by column chromatography (EE:hex=1:3). 158 mg (0.33 mmol, 35%) of a colorless foam is obtained.

Workup

  1. additionare added
  2. additionis diluted with EE
  3. washIt is washed once with water
  4. extractionthe aqueous phase is re-extracted twice with EE
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. customthe solvent is removed in vacuo
  7. customThe crude product is purified by column chromatography (EE:hex=1:3)

Sources & evidence

ORD record
ord-1e9d5c4ba6b842c2a95e1bece24b6ce2
Source dataset
uspto-grants-2016_08
Patent number
US09428497B2

Reaction notes

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