Ethanol → HCID 767282, compound

HRID 1747495Notes

Reaction equation

HRID 1747495 reaction equation
Cl.[CH2:2](N=C=NCCCN(C)C)[CH3:3].Cl.[N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[N:24]1[CH2:29][CH2:28][CH:27]([C:30]([OH:32])=[O:31])[CH2:26][CH2:25]1.C(O)C>CN(C1C=CN=CC=1)C.ClCCl>[N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[N:24]1[CH2:25][CH2:26][CH:27]([C:30]([O:32][CH2:2][CH3:3])=[O:31])[CH2:28][CH2:29]1

Participants

6

Reactant 3

HCID 702EthanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 56828036HCID 56828036, compound

Product 1

HCID 767282HCID 767282, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.79 g, 9.34 mmol) was added to a solution of 1-(quinolin-2-yl)piperidine-4-carboxylic acid hydrochloride (1.14 g, 3.89 mmol), N,N-dimethyl-4-aminopyridine (1.42 g, 11.6 mmol), and ethanol (546 μL, 9.34 mmol) in dichloromethane (20 mL), and the mixture was stirred overnight at room temperature. Then, the solvent in the reaction solution was distilled off under reduced pressure. A solution of the obtained residue in ethyl acetate was washed with water twice and brine once and dried over anhydrous sodium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=95/5-60/40 (gradient)] to obtain the title compound (1.07 g, yield: 96%).

Workup

  1. distillationThen, the solvent in the reaction solution was distilled off under reduced pressure
  2. washA solution of the obtained residue in ethyl acetate was washed with water twice
  3. dry with materialbrine once and dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=95/5-60/40 (gradient)]

Sources & evidence

ORD record
ord-d916b0b989cb4bec8f4ba39c25a4c5ab
Source dataset
uspto-grants-2015_10
Patent number
US09150575B2

Reaction notes

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