Dichloromethane → HCID 22100931, compound

HRID 1458365Notes

Reaction equation

HRID 1458365 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:18](Cl)(=[O:22])[C:19](Cl)=[O:20].Cl.Cl.[NH:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[CH2:28][CH2:27]1.C(Cl)Cl>C(OCC)(=O)C.C(N(CC)CC)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18](=[O:22])[C:19]([N:35]2[CH2:36][CH2:37][CH:32]([C:29]4[CH:28]=[CH:27][N:26]=[CH:31][CH:30]=4)[CH2:33][CH2:34]2)=[O:20])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 22100875Pyridine, 4-(4-piperidinyl)-, hydrochloride (1:2)HCID 22100925HCID 22100925, compound

Product 1

HCID 22100931HCID 22100931, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(3,5-dimethylphenyl)-1H-indole (200 mg in 2 mL dry methylene chloride) was added dropwise 0.083 mL oxalyl chloride and the mixture stirred at room temperature. After 1 hour, 213 mg 1,2,3,4,5,6-hexahydro-[4,4']bipyridinyl dihydrochloride was added followed by 1.5 mL methylene chloride and 0.567 mL triethylamine and the mixture continued stirring at room temperature. After 4 hours the reaction was diluted with ethyl acetate and washed sequentially with water, saturated aqueous ammonium chloride and brine. The organic portion was dried over sodium sulfate and the concentrate purified by flash chromatography on silica gel (methylene chloride:methanol, 96:4) to give the title compound (148 mg).

Workup

  1. stirringthe mixture continued stirring at room temperature
  2. washwashed sequentially with water, saturated aqueous ammonium chloride and brine
  3. dry with materialThe organic portion was dried over sodium sulfate
  4. customthe concentrate purified by flash chromatography on silica gel (methylene chloride:methanol, 96:4)

Sources & evidence

ORD record
ord-486bc19facc24dbba06c60338d74599b
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

Loading…