Ammonia → C-(5-(2-Chloro-phenoxy)-thiophen-2-yl)-methylamine

HRID 2080146Notes

Reaction equation

HRID 2080146 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:11][C:12]1[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=1[O:14][C:15]1[S:19][C:18]([C:20]#[N:21])=[CH:17][CH:16]=1.N.S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1>[Cl:11][C:12]1[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=1[O:14][C:15]1[S:19][C:18]([CH2:20][NH2:21])=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 24083Sulfuric acid magnesium salt (1:1)HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 231306225-(2-Chlorophenoxy)thiophene-2-carbonitrile

Product 1

HCID 23130405C-(5-(2-Chloro-phenoxy)-thiophen-2-yl)-methylamineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lithium aluminum hydride (1.79 g, 47.1 mmol) in tetrahydrofuran was added aluminum chloride (7.54 g, 56.5 mmol) on an ice bath, which was then stirred for 10 minutes. To the suspension was 5-(2-chloro-phenoxy)-thiophene-2-carbonitrile described in Preparation Example 158 (2.22 g, 9.42 mmol) was added on an ice bath, and the solution was stirred for 1 hour. An aqueous ammonia was added to the reaction solution, then, anhydrous magnesium sulfate was added for drying, and the solution was filtered through Celite pad. The filtrate was concentrated in vacuo, the residue was purified by NH silica gel column chromatography (heptane/ethyl acetate=1/2), and the title compound (2.26 g, 9.42 mmol, 100%) was obtained as a light brown oil.

Workup

  1. additionwas added on an ice bath
  2. stirringthe solution was stirred for 1 hour
  3. customfor drying
  4. filtrationthe solution was filtered through Celite pad
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by NH silica gel column chromatography (heptane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-1241c9b0889042f398c8e5162d4c5317
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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