Potassium Carbonate → HCID 71062035, compound

HRID 1774316Notes

Reaction equation

HRID 1774316 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:8].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N:31]2[CH2:36][CH2:35][N:34]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[O:8])[CH2:33][CH2:32]2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 220016181386927-90-7HCID 72545477HCID 72545477, compound

Product 1

HCID 71062035HCID 71062035, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 6-bromo-N-(2-pyridylmethyl)hexanamide (0.60 g, 2.1 mmol), 1-[2-(4-methoxyphenyl)phenyl]piperazine (0.68 g, 2.5 mmol) and K2CO3 (3.5 mmol) in acetonitrile was refluxed overnight. After cooling, the mixture was evaporated to dryness and H2O (20 mL) was added to the residue. The aqueous phase was extracted with AcOEt (2×30 mL). The collected organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was chromatographed (CHCl3/MeOH, 19:1, as eluent) to afford pure compound in 60% yield. 1H NMR (CDCl3): δ 1.35-1.42 (m, 2H), 1.53-1.63 (m, 2H), 1.68-1.78 (m, 2H), 2.28 (t, 2H, J=7.4 Hz), 2.42 (app. t, 2H), 2.65 (br s, 4H), 3.09 (br s, 4H), 3.81 (s, 3H), 4.45 (d, 2H, J=6.1 Hz), 6.12 (br t, 1H, D2O exchanged), 6.94 (d, 2H, J=8.8 Hz), 7.00 (d, 1H, J=8.0 Hz), 7.09-7.16 (m, 2H), 7.22-7.30 (m, 3H), 7.46 (d, 2H, J=8.8 Hz), 8.58 (m, 1H). GC-MS m/z 473 (M+1, 1), 472 (M+, 5), 379 (20), 282 (50), 226 (100), 210 (35).

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. customthe mixture was evaporated to dryness and H2O (20 mL)
  4. additionwas added to the residue
  5. extractionThe aqueous phase was extracted with AcOEt (2×30 mL)
  6. dry with materialThe collected organic layers were dried over Na2SO4
  7. customevaporated under reduced pressure
  8. customThe crude residue was chromatographed (CHCl3/MeOH, 19:1, as eluent)
  9. customto afford pure compound in 60% yield

Sources & evidence

ORD record
ord-c1ab2663133049b088c8ed2233b584bc
Source dataset
uspto-grants-2016_02
Patent number
US09260400B2

Reaction notes

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