Sodium Carbonate → Piperidine, 1-(2-phenylethyl)-

HRID 1007121Notes

Reaction equation

HRID 1007121 reaction equation
CC1(C)CC1C(N[CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=O.C1(C)C=CC(S(O[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30](NC(OC(C)(C)C)=O)=[CH:29][CH:28]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[I-].[Na+].C(#N)C>[CH2:25]([N:11]1[CH2:10][CH2:9][CH2:8][CH2:13][CH2:12]1)[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 113267772-(4-(Tert-butoxycarbonylamino)phenyl]ethyl-4-methylbenzenesulfonateHCID 22667753HCID 22667753, compound

Product 1

HCID 9513Piperidine, 1-(2-phenylethyl)-Yield 65.5%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

An acetonitrile (5 ml) solution of the piperidine compound (23:R=2,2-dimethylcyclopropane) (50 mg, 0.25 mmol) obtained in the process 1 of example 15 was added with 2-(4-t-butoxycarbonylaminophenyl)ethanol paratoluensulfonate (57 mg, 0.31 mmol), sodium carbonate (32 mg, 0.31 mmol) and sodium iodide (2 mg), which was in turn heated and refluxed at 100° C. for 2 hours. The resultant was extracted with ethyl acetate, and further washed with water and saturated saline solution, dried and vacuum concentrated, and then separately purified with a silica gel TLC plate (chloroform, methanol), thus obtained a phenethylpiperidine compound (31 mg, 29%).

Workup

  1. temperatureheated
  2. extractionThe resultant was extracted with ethyl acetate
  3. washfurther washed with water and saturated saline solution
  4. customdried
  5. concentrationvacuum concentrated
  6. customseparately purified with a silica gel TLC plate (chloroform, methanol)

Sources & evidence

ORD record
ord-28f767fbc4394ae896710491f8b8095b
Source dataset
uspto-grants-2004_09
Patent number
US06794378B2

Reaction notes

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