Piperidine → Tert-butyl 2-(2-(methoxymethoxy)-5-((piperidin-1-yl)methyl)benzamido)-4-phenylbenzoate

HRID 454645Notes

Reaction equation

HRID 454645 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:37][CH2:38][O:39][CH3:40])=[C:13]([CH:36]=1)[C:14]([NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:15]>CC(C)=O>[CH3:40][O:39][CH2:38][O:37][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:36][C:13]=1[C:14]([NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:15]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 66990849Tert-butyl 2-(5-(bromomethyl)-2-(methoxymethoxy)benzamido)-4-phenylbenzoate

Product 1

HCID 66990064Tert-butyl 2-(2-(methoxymethoxy)-5-((piperidin-1-yl)methyl)benzamido)-4-phenylbenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under ice-cooling, piperidine (0.094 mL) was added to an acetone (1.5 mL) suspension of tert-butyl 2-(5-(bromomethyl)-2-(methoxymethoxy)benzamido)-4-phenylbenzoate (0.10 g), followed by stirring at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-95% chloroform/methanol] to obtain 0.080 g of tert-butyl 2-(2-(methoxymethoxy)-5-((piperidin-1-yl)methyl)benzamido)-4-phenylbenzoate.

Workup

  1. temperatureUnder ice-cooling
  2. customThe solvent was evaporated under reduced pressure
  3. additiona saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the residue
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-95% chloroform/methanol]

Sources & evidence

ORD record
ord-b3d7d3b84a6e4a32986099206c7e2424
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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