Hydrazine hydrate (1:1) → 6-(2,2-Difluoro-2-phenylethoxy)-1-hexanamine

HRID 885526Notes

Reaction equation

HRID 885526 reaction equation
[F:1][C:2]([F:28])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>C(O)C>[F:1][C:2]([F:28])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH2:11]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 672458672-[6-(2,2-Difluoro-2-phenylethoxy)hexyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 509930806-(2,2-Difluoro-2-phenylethoxy)-1-hexanamineYield 54.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Intermediate 8 (6.41 g, 16.5 mmol) in ethanol (50 ml) was added hydrazine monohydrate (12 mL, 247 mmol). The mixture was stirred at room temperature overnight, concentrated, and the residue was triturated with isopropyl alcohol. The resulting solid was filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography with silica gel, eluting with methylene chloride/ethanol/ammonium hydroxide (80:8:1) to give the title compound (2.31 g, 54%) as oil.

Workup

  1. concentrationconcentrated
  2. customthe residue was triturated with isopropyl alcohol
  3. filtrationThe resulting solid was filtered
  4. customthe solvent removed under reduced pressure
  5. customThe residue was purified by column chromatography with silica gel
  6. washeluting with methylene chloride/ethanol/ammonium hydroxide (80:8:1)

Sources & evidence

ORD record
ord-17f235bf596f4d7b99caa78c7a8f508d
Source dataset
uspto-grants-2012_08
Patent number
US08242177B2

Reaction notes

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