Nitrogen → HCID 69429206, compound

HRID 1269459Notes

Reaction equation

HRID 1269459 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15](=[O:35])[NH:16][CH:17]1[C:26]2[C:21](=[CH:22][C:23](OS(C(F)(F)F)(=O)=O)=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N#N.C([O-])([O-])=O.[K+].[K+].[CH2:44]([N:47]1[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1)[CH:45]=[CH2:46]>CC#N.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15](=[O:35])[NH:16][CH:17]1[C:26]2[C:21](=[CH:22][C:23]([C:45]([CH2:44][N:47]3[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]3)=[CH2:46])=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

9

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 1397561-(2-Propenyl)piperidineHCID 72440627HCID 72440627, compound

Product 1

HCID 69429206HCID 69429206, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-[(6-trifluoromethanesulfonyloxy-1,2,3,4-tetrahydro-naphthalen-1-ylcarbamoyl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (624 mg, 1.19 mmol) in CH3CN (6 mL) was purged with N2, and then added palladium(II)acetate (Strem Chemicals, 20 mg, 0.09 mmol), 1,1′-bis(diphenylphosphino)ferrocene (Aldrich, 211 mg, 0.38 mmol), K2CO3 (Aldrich, 299 mg, 2.16 mmol) and 1-allylpiperidine (Lancaster, 904 mg, 7.22 mmol). The mixture was heated to 80° C. overnight, cooled to RT, diluted with water (10 mL), and extracted with ether. The organic solution was dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by silica gel chromatography (26% EtOAc-Hexane) to provide the title compound. MS (ESI): 496 (M+H)+.

Workup

  1. temperaturecooled to RT
  2. extractionextracted with ether
  3. dry with materialThe organic solution was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by silica gel chromatography (26% EtOAc-Hexane)

Sources & evidence

ORD record
ord-dc6d079b25d94c658edcd0a131ed3867
Source dataset
uspto-grants-2007_04
Patent number
US07199244B2

Reaction notes

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