Potassium Carbonate → HCID 67187631, compound

HRID 551784Notes

Reaction equation

HRID 551784 reaction equation
[N:1]1(NC(Cl)=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Cl.[Cl:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][Cl:22].[C:23](=O)([O-])[O-:24].[K+].[K+]>C(#N)C>[Cl:16][CH2:17][CH2:18][N:19]([CH2:20][CH2:21][Cl:22])[C:23]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 87302908HCID 87302908, compound

Product 1

HCID 67187631HCID 67187631, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 7 g of 3,4-dihydroquinoline-1(2H)-carbamic acid chloride in 180 ml of acetonitrile is introduced into a 500 ml round-bottomed flask. 9.6 g of bis(2-chloroethyl)amine hydrochloride and 14.83 g of potassium carbonate are subsequently added and the reaction mixture is stirred for 18 h. The acetonitrile is evaporated under reduced pressure and water and ethyl acetate are subsequently added. The aqueous phase is extracted with ethyl acetate and then the organic phases are combined, washed with water and dried over sodium sulfate and then the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a dichloromethane/methanol gradient from 1/0 to 95/5. 2.91 g of N,N-bis(2-chloroethyl)-3,4-dihydroquinoline-1(2H)-carboxamide are obtained.

Workup

  1. customThe acetonitrile is evaporated under reduced pressure and water and ethyl acetate
  2. additionare subsequently added
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. customThe residue is chromatographed on silica gel with a dichloromethane/methanol gradient from 1/0 to 95/5

Sources & evidence

ORD record
ord-6b7752ea3bf147eaa0eea57b59cd2397
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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