Triphenylphosphine → HCID 70166375, compound

HRID 1281732Notes

Reaction equation

HRID 1281732 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH:13]([N:16]1[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][CH2:17]1)([CH3:15])[CH3:14].O[C:24]1[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=1)[C:27]([O:29][CH2:30][CH3:31])=[O:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH:13]([N:16]1[CH2:21][CH2:20][CH:19]([O:22][C:24]2[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=2)[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:18][CH2:17]1)([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 24522Ethyl 3-hydroxybenzoateHCID 796811-Isopropylpiperidin-4-olHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 70166375HCID 70166375, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Diethyl azodicarboxylate (2.26 g) was added dropwise to a stirred mixture of N-isopropyl-4-hydroxypiperidine (Helv. Chim. Acta, 1966, 46, 693; 1.57 g), ethyl 3-hydroxybenzoate (1.66 g), triphenylphosphine (3.4 g) and THF (40 ml) which had been cooled to 0° C. The mixture was stirred at ambient temperature for 42 hours. The solvent was evaporated and the residue was partitioned between ethyl acetate and 2N aqueous hydrochloric acid. The aqueous phase was washed with ethyl acetate, basified to pH10 by the addition of solid potassium carbonate and extracted with diethyl ether. The organic extract was dried over magnesium sulphate and evaporated to give ethyl 3-(N-isopropypiperidin-4-yloxy)benzoate as an oil (1.53 g); NMR Spectrum: (CDCl3) 1.06 (d, 6H), 1.38 (t, 3H), 1.8 (m, 2H), 2.07 (m, 2H), 2.41 (m, 2H), 2.72 (m, 1H), 2.78 (m, 2H), 4.38 (m, 2H), 7.08 (m, 1H), 7.32 (t, 1H), 7.57 (d, 1H), 7.62 (d, 1H). The oil so obtained was dissolved in diethyl ether (20 ml) and a 1M solution of hydrogen chloride in diethyl ether (12 ml) was added. The resultant precipitate was isolated to give ethyl 3-(N-isopropypiperidin-4-yloxy)benzoate hydrochloride salt (1.55 g).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and 2N aqueous hydrochloric acid
  3. washThe aqueous phase was washed with ethyl acetate
  4. additionbasified to pH10 by the addition of solid potassium carbonate
  5. extractionextracted with diethyl ether
  6. extractionThe organic extract
  7. dry with materialwas dried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-07983fe3ef7f4cc0a59dcb8c9b6b7c30
Source dataset
uspto-grants-2002_09
Patent number
US06455520B1

Reaction notes

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