Aluminium lithium hydride → C-(2-phenoxymethyl-benzofuran-5-yl)-methylamine

HRID 1171221Notes

Reaction equation

HRID 1171221 reaction equation
[O:1]([CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:12]=2[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[O:1]([CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][C:12]=2[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 687149782-Phenoxymethyl-benzofuran-5-carbonitrile

Product 1

HCID 57608260C-(2-phenoxymethyl-benzofuran-5-yl)-methylamineYield 47.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran (1 mL) solution of 2-phenoxymethyl-benzofuran-5-carbonitrile (25 mg, 0.1 mmol) described in Production Example 75-1-2 was dropped into a tetrahydrofuran (5 mL) suspension of lithium aluminum hydride (19 mg, 0.5 mmol). This mixture was stirred at room temperature for 3 hours and 45 minutes. After adding ice water to the reaction mixture and stirring, insoluble matter was filtered out through Celite followed by rinsing with ethyl acetate. The organic layer was separated followed by washing with sat. NaCl, drying over anhydrous magnesium sulfate and concentrating under a reduced pressure to obtain the title compound (12 mg, 47%).

Workup

  1. stirringstirring
  2. filtrationinsoluble matter was filtered out through Celite
  3. washby rinsing with ethyl acetate
  4. customThe organic layer was separated
  5. washby washing with sat. NaCl
  6. dry with materialdrying over anhydrous magnesium sulfate
  7. concentrationconcentrating under a reduced pressure

Sources & evidence

ORD record
ord-97a9d4044dba41b9a993229c165d86ba
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

Loading…