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

HRID 1966618Notes

Reaction equation

HRID 1966618 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-6e4c1e03f23a4acf8d26a15015c6bd01
Source dataset
uspto-grants-2013_04
Patent number
US08420669B2

Reaction notes

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