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

HRID 1033368Notes

Reaction equation

HRID 1033368 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-9f11e4888cdb48fd874f7f681e5f2ff0
Source dataset
uspto-grants-1994_05
Patent number
US05310743

Reaction notes

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