Methyl chloroformate → HCID 22611286, compound

HRID 725979Notes

Reaction equation

HRID 725979 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1.Cl[C:19]([O:21][CH3:22])=[O:20]>ClCCl>[CH3:22][O:21][C:19]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1)=[O:20]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 118312203-(1-Methylpiperidin-4-yl)-1h-indol-5-amine

Product 1

HCID 22611286HCID 22611286, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 10 mg (0.0437 mMol) 5-amino-3-(1-methyl-piperidin-4-yl)-1H-indole and 15.0 mg (0.131 mMol) polyvinyl-pyridine in 3.0 mL dichloromethane were added 4.3 mg (0.0458 mMol) methyl chloroformate. The reaction mixture was mixed for 18 hours at ambient temperature. To this mixture were then added 170 mg (0.137 mMol) aminomethylated polystyrene and the reaction mixed for an additional 18 hours. The reaction mixture was then filtered and the volatiles evaporated to give 10.2 mg (81%) of the title compound.

Workup

  1. additionThe reaction mixture was mixed for 18 hours at ambient temperature
  2. additionTo this mixture were then added 170 mg (0.137 mMol)
  3. additionthe reaction mixed for an additional 18 hours
  4. filtrationThe reaction mixture was then filtered
  5. customthe volatiles evaporated

Sources & evidence

ORD record
ord-279595d7cef54207b81c96506bafd69a
Source dataset
uspto-grants-1998_01
Patent number
US05708008

Reaction notes

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