Methanol → 1-{4-[(3-Fluorobenzyl)oxy]phenyl}methanamine

HRID 2080042Notes

Reaction equation

HRID 2080042 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[CH2:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1.CO.[Cl-].[NH4+]>O1CCCC1.O>[F:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[CH2:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 22293834-[(3-Fluorophenyl)methoxy]benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 167723641-{4-[(3-Fluorobenzyl)oxy]phenyl}methanamineYield 935.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Next, to a solution of lithium aluminum hydride (1.25 g, 133.0 mmol) in tetrahydrofuran (15 mL) was added a solution of 4-(3-fluorobenzyloxy)-benzonitrile (218 mg, 0.615 mmol) in tetrahydrofuran (12 mL) on an ice bath, and the solution was stirred at room temperature for 19 hours. A mixture solvent of methanol and water (9:1) was added to the reaction solution, an aqueous solution of saturated ammonium chloride was further added, and the solution was stirred on an ice bath for 30 minutes. This solution was filtered through Celite pad, and insoluble matter was removed. The filtrate was partitioned, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated, and the title compound (1.33 g, 44%) was obtained as a yellow solid. This was used in the next reaction without further purification.

Workup

  1. stirringthe solution was stirred on an ice bath for 30 minutes
  2. filtrationThis solution was filtered through Celite pad, and insoluble matter
  3. customwas removed
  4. customThe filtrate was partitioned
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-78c838c858be45288131ab606374a892
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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