Ammonia methanol → C-(4-(3-Fluorophenoxy)thiophen-2-yl)methylamine

HRID 2080074Notes

Reaction equation

HRID 2080074 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[CH:7]=[C:8]([CH:11]=O)[S:9][CH:10]=1.[NH3:16].CO>[Ni]>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[CH:7]=[C:8]([CH2:11][NH2:16])[S:9][CH:10]=1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 231306054-(3-Fluorophenoxy)thiophene-2-carbaldehyde

Product 1

HCID 23130348C-(4-(3-Fluorophenoxy)thiophen-2-yl)methylamine

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

4-(3-Fluorophenoxy)thiophene-2-carbaldehyde described in Preparation Example 34 (210 mg, 0.95 mmol) was dissolved in 7N ammonia/methanol (30 mL), Raney nickel (500 mg) was added thereto, followed by stirring for 19 hours under hydrogen atmosphere at room temperature. The reaction mixture was filtered through Celite pad, Raney nickel was removed, silica gel was added to the filtrate, then, the solvent was evaporated in vacuo, for adsorption on silica gel, purification by silica gel chromatography (ethyl acetate, then ethyl acetate:methanol=4:1) was carried out, and the title compound (70 mg, 0.32 mmol) was obtained as a pale yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite pad, Raney nickel
  2. customwas removed
  3. additionsilica gel was added to the filtrate
  4. customthe solvent was evaporated in vacuo, for adsorption on silica gel, purification by silica gel chromatography (ethyl acetate

Sources & evidence

ORD record
ord-f95805fe0eb14dd091f8d25adb31af23
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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