N-(2-Aminoethyl)piperidine → HCID 57934067, compound

HRID 1950317Notes

Reaction equation

HRID 1950317 reaction equation
C(NC1C=C(OC)C=CC=1C1CCC2C(=CC=C(OC)C=2)C1)C.BrC1C=CC(C(Cl)=O)=CC=1.Br[C:35]1[CH:65]=[CH:64][C:38]([C:39]([N:41]([CH2:62][CH3:63])[C:42]2[CH:47]=[C:46]([O:48][CH3:49])[CH:45]=[CH:44][C:43]=2[CH:50]2[CH2:59][CH2:58][C:57]3[C:52](=[CH:53][CH:54]=[C:55]([O:60][CH3:61])[CH:56]=3)[CH2:51]2)=[O:40])=[CH:37][CH:36]=1.[NH2:66][CH2:67][CH2:68][N:69]1[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]1.CC(C)([O-])C.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:62]([N:41]([C:42]1[CH:47]=[C:46]([O:48][CH3:49])[CH:45]=[CH:44][C:43]=1[CH:50]1[CH2:59][CH2:58][C:57]2[C:52](=[CH:53][CH:54]=[C:55]([O:60][CH3:61])[CH:56]=2)[CH2:51]1)[C:39](=[O:40])[C:38]1[CH:64]=[CH:65][C:35]([NH:66][CH2:67][CH2:68][N:69]2[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]2)=[CH:36][CH:37]=1)[CH3:63]

Participants

9

Reactant 5

HCID 33944N-(2-Aminoethyl)piperidineHCID 685154-Bromobenzoyl chlorideHCID 23087318Ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amineHCID 23676156Sodium t-butoxideHCID 66626256HCID 66626256, compound

Product 1

HCID 57934067HCID 57934067, compound

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Synthesized from ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine and 4-bromobenzoyl chloride according to an analogous synthetic method to Preparation Example 86, to a suspension of the resulting 4-bromo-N-ethyl-N-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]benzamide (299 mg) in 1,4-dioxane (10 ml) were sequentially added 1-(2-aminoethyl)piperidine (0.13 ml), sodium tert-butoxide (88 mg), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (23 mg) and tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (13 mg), and the solution was stirred overnight at 100° C. The solution was let to cool, then the insoluble material was filtered through celite pad, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate-tetrahydrofuran system) to provide the title compound (253 mg).

Workup

  1. temperatureto cool
  2. filtrationthe insoluble material was filtered through celite pad
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate-tetrahydrofuran system)

Sources & evidence

ORD record
ord-d0a10792db2e45f99a79978e809e02d2
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

Loading…