3,5-Dimethylbenzoyl Chloride → HCID 57163883, compound

HRID 1737067Notes

Reaction equation

HRID 1737067 reaction equation
[C:1]([NH:4][C@H:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13]CC2C=CC=CC=2)=O)[C@@H:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:6]1)(=[O:3])[CH3:2].[H][H].[CH3:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([CH3:39])[CH:38]=1)C(Cl)=O>C(O)C.Cl.[Pd]>[C:1]([NH:4][C@H:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:13])[C:32]2[CH:36]=[C:37]([CH3:39])[CH:38]=[C:30]([CH3:29])[CH:31]=2)[C@@H:7]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 810883,5-Dimethylbenzoyl ChlorideHCID 57040483HCID 57040483, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57163883HCID 57163883, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 496 mg (1.41 mmol) of (2R*,4S*)-N-acetyl-1-benzyloxycarbonyl-2-phenyl-4-piperidinamine in 30 ml of ethanol and 8 ml of 1N hydrochloric acid is mixed with 50 mg of 10% Pd/C catalyst and stirred under a hydrogen atmosphere until no more hydrogen is taken up. The catalyst is removed by filtration through diatomaceous earth, and the filtrate is evaporated to dryness under reduced pressure. The residue is taken up in 5 ml of dichloromethane and 5 ml of 10% strength aqueous sodium bicarbonate solution and, while stirring at 0°, 285 mg (1.69 mmol) of 3,5-dimethylbenzoyl chloride are added slowly over the course of 1 hour. The reaction mixture is extracted with dichloromethane. The organic phase is separated off, dried over sodium sulfate and evaporated to dryness under reduced pressure. The title compound crystallises from ethyl acetate; melting point 201°-203°; CI-MS: (M+H)+=351.

Workup

  1. customThe catalyst is removed by filtration through diatomaceous earth
  2. customthe filtrate is evaporated to dryness under reduced pressure
  3. extractionThe reaction mixture is extracted with dichloromethane
  4. customThe organic phase is separated off
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe title compound crystallises from ethyl acetate

Sources & evidence

ORD record
ord-94bc82b442664e3fa41cd32c170f4cd2
Source dataset
uspto-grants-1996_07
Patent number
US05541195

Reaction notes

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