Cyclohexene → 4-(2-Methoxyphenyl)piperidine

HRID 2256029Notes

Reaction equation

HRID 2256029 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C1CCCCC=1>C(O)C.[Pd].CCOCC>[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1

Participants

6

Reactant 2

HCID 8079CyclohexeneHCID 21839784HCID 21839784, compound

Product 1

HCID 5447384-(2-Methoxyphenyl)piperidineYield 50.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-benzyloxycarbonyl-4-(2-methoxyphenyl)piperidine (0.67 g) in ethanol (10 mL) was treated with cyclohexene (4.2 mL) followed by 10% palladium on carbon (0.13 g). After heating to reflux for 2 hours, the reaction mixture was cooled to room temperature, diluted with ether and extracted with 1N hydrochloric acid. The aqueous layer was made basic with sodium bicarbonate and extracted with dichloromethane. The organic layers were dried over anhydrous sodium sulfate and evaporated to afford the piperidine (0.2 g); NMR (CDCl3): 1.60 (d of q, 2, J1 =12, J2 =4), 1.73-1.82 (broad, 2), 2.74-2.83 (d of t, 2, J1 =12, J2 =2), 3.02-3.2 (m, 3), 3.82 (s, 3), 6.85 (d, 1, J=8), 6.9 (m, 1), 7.15-7.26 (m, 2); MS: m/z=192(M+1). This material was used in the next step without further purification.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 2 hours
  3. extractionextracted with 1N hydrochloric acid
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-b10a2cfd3fb2447bab7c94695cb42a1a
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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