Toluene → HCID 68701220, compound

HRID 2245860Notes

Reaction equation

HRID 2245860 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1.[CH2:22]([N:25]1[CH2:30][C@@H:29]([CH3:31])[NH:28][CH2:27][C@@H:26]1[CH3:32])[CH:23]=[CH2:24].C1(C)C=CC=CC=1>C(N(CC)CC)C>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][CH:12]=[C:3]([C@@H:1]([N:28]2[CH2:27][C@@H:26]([CH3:32])[N:25]([CH2:22][CH:23]=[CH2:24])[CH2:30][C@@H:29]2[CH3:31])[N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]=[N:14]2)[CH:4]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 639145Methyl 3-formylbenzoateHCID 11291191(2S,5R)-1-allyl-2,5-dimethylpiperazineHCID 178418385HCID 178418385, compound

Product 1

HCID 68701220HCID 68701220, compoundYield 109.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Methyl 3-formylbenzoate (10 g, 60.91 mmol, 1 eq), benzotriazole (7.25 g, 60.91 mmol, 1 eq) and (2S,5R)-1-allyl-2,5-dimethylpiperazine (Chirotech Division of Dow Pharmaceutical Services, Cambridge, UK, 9.39 g, 60.91 mmol, 1 eq) were placed in a flask with dry toluene (300 mL) and triethylamine (1 mL). The flask was fitted with a Dean-Stark trap and condenser and heated to a gentle reflux in an oil bath (temperature ≦135° C.) for several hours with azeotropic removal of water. Most of the toluene was removed under reduced pressure to give 28 g of crude 3-[(S)-((2S,5R)-4-allyl-2,5-dimethylpiperazin-1-yl)benzotriazol-1-yl-methyl]benzoic acid methyl ester as a dark amber viscous liquid.

Workup

  1. customThe flask was fitted with a Dean-Stark trap and condenser
  2. temperatureheated to
  3. temperaturea gentle reflux in an oil bath (temperature ≦135° C.) for several hours
  4. customwith azeotropic removal of water
  5. customMost of the toluene was removed under reduced pressure

Sources & evidence

ORD record
ord-6594005468734b2c9f17d66f1b7b3dd3
Source dataset
uspto-grants-2010_03
Patent number
US07683168B2

Reaction notes

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