Hydrazine hydrate (1:1) → HCID 59652050, compound

HRID 2042647Notes

Reaction equation

HRID 2042647 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=O)[CH2:22][CH2:23][C:24](OCC)=[O:25])=[C:17]([F:30])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:32][NH2:33]>C(O)(C)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH2:22][CH2:23][C:24](=[O:25])[NH:33][N:32]=3)=[C:17]([F:30])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59652041HCID 59652041, compound

Product 1

HCID 59652050HCID 59652050, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a 250 mL round bottom flask, 4-[4-(3-ethoxycarbonyl-propionyl)-3-fluoro-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (4.1 g, 9.68 mmol), and hydrazine monohydrate (0.97 mL, 19.4 mmol), in isopropanol (100 mL) was heated to reflux 14 h. The reaction was cooled and the solvent concentrated under vacuum. Purification with silica gel chromatography eluting with methylene chloride/methanol (95:5) produced 945 mg (25%). Mp 146-148° C. MS m/z 392 (M+H).

Workup

  1. temperatureto reflux 14 h
  2. temperatureThe reaction was cooled
  3. concentrationthe solvent concentrated under vacuum
  4. customPurification with silica gel chromatography
  5. washeluting with methylene chloride/methanol (95:5)
  6. customproduced 945 mg (25%)

Sources & evidence

ORD record
ord-1ffd6b96a49d4cf59191d8086d17217a
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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