Acetonitrile → (2R*,4S*)-2-(4-chlorobenzyl)-1-(3,5-dimethylbenzoyl)-N-acetyl-4-piperidinamine

HRID 1737065Notes

Reaction equation

HRID 1737065 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[C:6]([O:9]C(=O)C)(=O)[CH3:7].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([N:25]([CH2:36]OCC)[C:26](=[O:35])[C:27]2[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=2)[CH2:22][CH:23]=[CH2:24])=[CH:16][CH:15]=1.C(=O)(O)[O-].[Na+].C(#[N:47])C>>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][C@@H:21]2[CH2:22][C@@H:23]([NH:47][C:6](=[O:9])[CH3:7])[CH2:24][CH2:36][N:25]2[C:26](=[O:35])[C:27]2[CH:28]=[C:29]([CH3:34])[CH:30]=[C:31]([CH3:33])[CH:32]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 7918Acetic AnhydrideHCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 19035912N-{5-(4-Chlorophenyl)pent-1-en-4-yl}-N-ethoxymethyl-3,5-dimethylbenzamide

Product 1

HCID 57050444(2R*,4S*)-2-(4-chlorobenzyl)-1-(3,5-dimethylbenzoyl)-N-acetyl-4-piperidinamine

Procedure

0.61 ml of tin tetrachloride and 0.24 ml of acetic anhydride are added successively to a solution of 1.0 g of N-{5-(4-chlorophenyl)pent-1-en-4-yl}-N-ethoxymethyl-3,5-dimethylbenzamide in acetonitrile cooled to -20°. The reaction mixture is then stirred at -20° for 2 hours and at 25° for 1 hour, poured into saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic phase is separated off, dried over sodium sulfate and evaporated to dryness under reduced pressure. The crude title compound (orange oil) is purified by chromatography on silica gel with dichloromethane/methanol/25% strength ammonia solution (95:5:0.1) as mobile phase. TLC (dichloromethane/methanol/25% strength ammonia solution; 90:10:0.1): Rf =0.45; FD-MS: M+=398

Workup

  1. temperaturecooled to -20°
  2. extractionextracted with ethyl acetate
  3. customThe organic phase is separated off
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe crude title compound (orange oil) is purified by chromatography on silica gel with dichloromethane/methanol/25% strength ammonia solution (95:5:0.1) as mobile phase

Sources & evidence

ORD record
ord-7d30eb57694d44d9967eb38c24ab2a34
Source dataset
uspto-grants-1996_07
Patent number
US05541195

Reaction notes

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