Acetonitrile → HCID 49850513, compound

HRID 403117Notes

Reaction equation

HRID 403117 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.CO[CH:30]1[CH2:35][CH:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:33][CH2:32]N1.[C:42]([O-:45])([O-])=O.[K+].[K+].[CH3:48]C#N>>[C:24]([O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][N:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH:39]1[CH2:38][CH2:37][CH:36]([C:34]2[CH:33]=[CH:32][CH:48]=[CH:30][C:35]=2[O:45][CH3:42])[CH2:41][CH2:40]1)([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 671282442-Methoxy-4-phenylpiperidineHCID 866726866-bromo-N-(2-tert-butoxybenzyl)-N-(pyridin-2-ylmethyl)hexan-1-amine

Product 1

HCID 49850513HCID 49850513, compoundYield 58%

Procedure

The compound 10 (0.377 g, 0.85 mmol), 2-methoxy-4-phenylpiperidine (0.262 g, 1.54 mmol) and K2CO3 (0.118 g, 0.85 mmol) were added to 50 mL CH3CN, and the solution was refluxed under argon atmosphere for 6 h and stirred overnight. Then the solvent was evaporated to dryness. Purification was carried out on a silica gel TLC plate that was developed in 4% methanolic NH3 (7 M NH3 in methanol)/96% CH2Cl2. The product was obtained as pale yellow oil (58%). 1H NMR (CDCl3) δ 8.491 (d, 1H, Ar), 7.262 (m, 1H, Ar), 7.583 (m, 2H, Ar), 7.216 (d, 1H, Ar), 7.160 (m, 1H, Ar), 7.112 (m, 2H, Ar), 7.024 (m, 2H, Ar), 6.917 (t, 1H, Ar), 6.839 (d, 1H, Ar), 3.806 (s, 3H, —OCH3), 3.744 (s, 2H, —CH2—), 3.667 (s, 2H, —CH2—), 3.043 (d, 2H, —CH2—), 2.958 (m, 1H, —CH—), 2.459 (t, 2H, —CH2—), 2.326 (m, 2H, —CH2—), 2.061 (m, 2H, —CH2—), 1.790 (m, 4H, —CH2—CH2—), 1.531 (m, 4H, —CH2—CH2—), 1.360 (s, 9H, —C(CH3)3—), 1.298 (m, 2H, —CH2—), 1.228 (m, 2H, —CH2—). Mass Spec.=543.78 (M+H)+.

Workup

  1. temperaturethe solution was refluxed under argon atmosphere for 6 h
  2. customThen the solvent was evaporated to dryness
  3. customPurification

Sources & evidence

ORD record
ord-8bceeb1c7350482e8ae5f3fd694f4063
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

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