Thionyl Chloride → 3-(4-Methylpiperazine-1-carbonyl)-7-oxa-bicyclo[2,2,1]heptane-2-carbonyl chloride

HRID 45178Notes

Reaction equation

HRID 45178 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([CH:10]2[CH:15]3[O:16][CH:12]([CH2:13][CH2:14]3)[CH:11]2[C:17]([OH:19])=O)=[O:9])[CH2:4][CH2:3]1.S(Cl)([Cl:22])=O>C(Cl)Cl.CN(C=O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([CH:10]2[CH:15]3[O:16][CH:12]([CH2:13][CH2:14]3)[CH:11]2[C:17]([Cl:22])=[O:19])=[O:9])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 35785723-(4-Methylpiperazine-1-carbonyl)-7-oxabicyclo(2.2.1)heptane-2-carboxylic acid

Product 1

HCID 591730493-(4-Methylpiperazine-1-carbonyl)-7-oxa-bicyclo[2,2,1]heptane-2-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of 3-(4-methylpiperazine-1-carbonyl)-7-oxa-bicyclo[2,2,1]-heptane-2-carboxylic acid (938 mg, 3.5 mmole) in methylene chloride (30 mL) was added thionyl chloride (1 mL) followed by a few drops of DMF. After stirring at ice-cold temperature for 30 min, the ice-bath was removed and stirring continued at room temperature overnight. The excess thionyl chloride was removed using oil-free vacuum pump at −50° C. and to the residue was added methylene chloride (10 mL). The resulted thin slurry of 1 was used as such in the next reaction.

Workup

  1. customthe ice-bath was removed
  2. stirringstirring
  3. waitcontinued at room temperature overnight
  4. customThe excess thionyl chloride was removed
  5. customat −50° C.
  6. additionto the residue was added methylene chloride (10 mL)
  7. customsuch in the next reaction

Sources & evidence

ORD record
ord-94b494dbcac74e5881890d97e70fea87
Source dataset
uspto-grants-2013_09
Patent number
US08541458B2

Reaction notes

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