Isopropylamine → HCID 44211251, compound

HRID 52090Notes

Reaction equation

HRID 52090 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[C:5](N1C=CN=C1)(N1C=CN=C1)=[O:6].[N:17]1([CH2:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]([O:30][CH2:31]/[CH:32]=[CH:33]\[CH2:34][NH2:35])[CH:25]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C(Cl)Cl>[N:17]1([CH2:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]([O:30][CH2:31]/[CH:32]=[CH:33]\[CH2:34][NH:35][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH:25]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 136724732-Buten-1-amine, 4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-, (Z)-

Product 1

HCID 44211251HCID 44211251, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 0.113 g of isopropylamine in 2 ml of methylene chloride was added to a solution of 0.31 g of carbonyldiimidazole in 5 ml of methylene chloride, and the resulting mixture was cooled with ice, after which a solution of 0.500 g of 4-(4-piperidinomethyl-2-pyridyloxy) -cis-2-butenylamine in 5 ml of methylene chloride was added. The reaction mixture was stirred at room temperature for 2 hours, after which it was poured into ice-water and extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:20 by volume mixture of methanol and ethyl acetate as the eluent, to give 0.41 g (yield 62%) of the title compound as a white powder, melting at 90°-92° C.

Workup

  1. temperaturethe resulting mixture was cooled with ice
  2. extractionextracted with methylene chloride
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by column chromatography through silica gel
  6. additionby volume mixture of methanol and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-8cc93bdbcd6b4d72bb39636f089020c1
Source dataset
uspto-grants-1997_04
Patent number
US05616579

Reaction notes

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