Diethyl Ether → HCID 22097666, compound

HRID 1087496Notes

Reaction equation

HRID 1087496 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([O:20][CH2:21][CH3:22])C>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([OH:17])([C:2]2[CH:1]=[CH:22][C:21]([O:20][CH3:18])=[CH:4][CH:3]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 3283Diethyl EtherHCID 643496Benzyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 22097666HCID 22097666, compound

Procedure

mixture to a temperature of about 20° C., a solution of N-benzyloxycarbonyl-4-piperidone (48.2 g) in ethyl ether (450 cc) is poured in. Stirring is continued for 15 hours at this temperature. The reaction medium is then hydrolysed with a saturated solution of ammonium chloride to pH 6-7, the extracted with diethyl ether (3×500 cc). The organic phase is dried over anhydrous magnesium sulphate and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa). The residual oil is purified by flash-chromatography on a silica column, under a current of argon at medium pressure (0.5-1.5 bar) with dichloromethane and then a mixture of dichloromethane and methanol (90-10 vol) as eluant. N-Benzyloxycarbonyl-4-hydroxy-4-(4-methoxyphenyl)piperidine (21.2 g), m.p. 98° C. is thus obtained, which is used in the crude state in the subsequent syntheses.

Workup

  1. extractionhydrolysed with a saturated solution of ammonium chloride to pH 6-7, the extracted with diethyl ether (3×500 cc)
  2. dry with materialThe organic phase is dried over anhydrous magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa)
  4. customThe residual oil is purified by flash-chromatography on a silica column
  5. additionunder a current of argon at medium pressure (0.5-1.5 bar) with dichloromethane and then a mixture of dichloromethane and methanol (90-10 vol) as eluant

Sources & evidence

ORD record
ord-a3ff8cacaf8742abaaf5d96daa563897
Source dataset
uspto-grants-1991_07
Patent number
US05036075

Reaction notes

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