Ammonium Hydroxide → [2-(4-Fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butyl]amine

HRID 749469Notes

Reaction equation

HRID 749469 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[C:9]#[N:10])=[C:4]([CH3:20])[CH:3]=1.[NH4+].[OH-]>C(O)C.O.[Ni]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:9][NH2:10])=[C:4]([CH3:20])[CH:3]=1

Participants

6

Reactant 2

HCID 14923Ammonium HydroxideHCID 689763902-(4-fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butanenitrile

Product 1

HCID 68976391[2-(4-Fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butyl]amineYield 91.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-(4-Fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butanenitrile (4.5 g, 16 mmol) was dissolved in ethanol (40 mL) and concentrated NH4OH aq (20 mL). Raney® nickel suspended in water (one teaspoonful) was added and the mixture was alternately evacuated and flushed with H2. The mixture was then stirred under H2 at room temperature until the consumption of gas ceased. The catalyst was removed with a magnet and the mixture was then filtrated and the solvent was evaporated. There was obtained 4.1 g (90%) of [2-(4-fluoro-2-methylphenyl)-4(tetrahydro-2H-pyran-2-yloxy)butyl]amine as a pale blue oil. 1H NMR (500 MHz, CDCl3): 1.4-2.0 (m, 8H), 2.4 (d, 3H), 3.2-3.8 (m, 6H), 4.4-4.6 (d, 1H), 6.9 (d, 2H), 7.1-7.2 (b, 1H).

Workup

  1. additionwas added
  2. customthe mixture was alternately evacuated
  3. customflushed with H2
  4. customThe catalyst was removed with a magnet
  5. filtrationthe mixture was then filtrated
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-dc8f214e49854b0caa4f948e0cbc3347
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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