Dichloromethane → 1,4-Benzenedimethanamine

HRID 1595173Notes

Reaction equation

HRID 1595173 reaction equation
Cl[C:2]1[C:7]([C:8](O)=O)=[CH:6][C:5](OC[C@@H]2CCN2)=[CH:4][N:3]=1.[CH:17]1([N:23]=C=NC2CCCCC2)CCCCC1.[CH2:32](Cl)Cl>>[NH2:23][CH2:17][C:4]1[CH:5]=[CH:6][C:7]([CH2:2][NH2:3])=[CH:8][CH:32]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 10933676HCID 10933676, compound

Product 1

HCID 683151,4-Benzenedimethanamine

Procedure

A solution of (S)-2-chloro-3-carboxy-5-(2-azetidinylmethoxy)pyridine 10 (R1=Cl and n=1) (2 mmol) and the linker molecule 1,4-bisaminomethylbenzene (1 mmol) in CH2Cl2 (5 mL) is prepared under argon in a flask equipped with magnetic stirrer and a drying tube. To this solution is added dicyclohexylcarbodiimide (solid, 2.2 mmol). The progress of the reaction is followed by tlc and after reaction occurs, the reaction solution is quenched in water, aqueous sodium bicarbonate is added and the aqueous mixture is extracted with methylene chloride. The organic layer is washed with aqueous Na2CO3 and with H2O, dried (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. The desired compound 39 (where R1=Cl and n=1) is obtained by purification of the crude product with the use of HPLC.

Workup

  1. customequipped with magnetic stirrer and a drying tube
  2. customafter reaction
  3. customthe reaction solution is quenched in water
  4. additionaqueous sodium bicarbonate is added
  5. extractionthe aqueous mixture is extracted with methylene chloride
  6. washThe organic layer is washed with aqueous Na2CO3 and with H2O
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give the crude product

Sources & evidence

ORD record
ord-381a674dea5f4d2aaa51c896eceeb1a2
Source dataset
uspto-grants-2001_09
Patent number
US06288055B1

Reaction notes

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