Water → C-(5-(3-Benzyloxy-phenoxy)-thiophen-2-yl)-methylamine

HRID 2080060Notes

Reaction equation

HRID 2080060 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:26]=[CH:27][CH:28]=1)[O:18][C:19]1[S:23][C:22]([C:24]#[N:25])=[CH:21][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>O1CCCC1>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:26]=[CH:27][CH:28]=1)[O:18][C:19]1[S:23][C:22]([CH2:24][NH2:25])=[CH:21][CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 231303925-(3-Benzyloxy-phenoxy)-thiophene-2-carbonitrile

Product 1

HCID 23130639C-(5-(3-Benzyloxy-phenoxy)-thiophen-2-yl)-methylamineYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Next, to a solution of lithium aluminum hydride (27 mg, 0.716 mmol) in tetrahydrofuran (2.0 mL) was added a solution of 5-(3-benzyloxy-phenoxy)-thiophene-2-carbonitrile obtained above (110 mg, 0.358 mmol) in tetrahydrofuran (1 mL), and the solution was stirred at room temperature for 3 hours. Water was added to the reaction solution, which was then extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain the title compound (80 mg, 72%) as a red solid. This compound was used in the next reaction without purification.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7e9b5442dffe4c5ba945897bbcac4381
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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