Potassium Carbonate → HCID 70300686, compound

HRID 1418726Notes

Reaction equation

HRID 1418726 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])OC(C)(C)C)[CH2:3][CH2:2]1.Cl[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:33](=[O:36])([O-])[O-].[K+].[K+]>CN(C)C=O>[C:21]1([CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19]/[CH:18]=[CH:17]\[CH2:16][N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:36][C:33]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:5][CH2:6]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 70031862HCID 70031862, compound

Product 1

HCID 70300686HCID 70300686, compoundYield 133.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred suspension of 1.16 g (5.78 mmol) of 4-piperidinylcarbamic acid, 1,1-dimethylethyl ester (Example 1 Part B), 1.35 g (5.26 mmol) of (Z)-1-chloro-5,5-diphenyl-2-pentene, and 799 mg (5.78 mmol) of potassium carbonate in 15 mL of N,N-dimethylformamide was heated to 60° C. for eighteen hours, cooled, filtered and concentrated to a dark oil which was chromatographed on silica gel (150 g) eluted with 95:5 methylene chloride/methanol to provide 1.82 g (82%) of title compound, as an off-white solid.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationconcentrated to a dark oil which
  4. customwas chromatographed on silica gel (150 g)
  5. washeluted with 95:5 methylene chloride/methanol

Sources & evidence

ORD record
ord-0a76f9e7c7034e75a57fbe15d2daffee
Source dataset
uspto-grants-1999_03
Patent number
US05883099

Reaction notes

Loading…