Dicyclohexylcarbodiimide → N-(1-phenyl-3-piperidinopropyl)quinaldinamide

HRID 34998Notes

Reaction equation

HRID 34998 reaction equation
[N:1]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:2]=1[CH2:3][C:4]([OH:6])=O.C1C(=O)N(O)C(=O)C1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:38][CH:39]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>C(OCC)(=O)C>[C:48]1([CH:39]([NH:38][C:4]([CH2:3][C:2]2[CH:7]=[CH:8][C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:1]=2)=[O:6])[CH2:40][CH2:41][N:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 47117842-(Quinolin-2-YL)acetic acidHCID 137990911-Phenyl-3-(piperidin-1-yl)propan-1-amine

Product 1

HCID 67930081N-(1-phenyl-3-piperidinopropyl)quinaldinamideYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of 866 mg (5.0 mmol.) of quinaldinic acid and 576 mg (5.0 mmol.) of 1-hydroxysuccinimide in 20 ml of ethyl acetate was dropwise added over a period of 5-10 min. under chilling with ice a solution of 1.09 g (5.0 mmol.) of N,N'-dicyclohexylcarbodiimide. After the addition was complete, the mixture was stirred for 2 hours at room temperature. To this mixture was dropwise added a solution of 1.09 g (5.0 mmol.) of 1-(3-amino-3-phenylpropyl)piperidine in 5 ml of ethyl acetate. After the addition was complete, the mixture was stirred overnight at room temperature. Precipitated insolubles were filtered off and then the insolubles were washed with ethyl acetate. The filtrate and the washings were combined and washed twice with a saturated aqueous sodium hydrogencarbonate solution and once with a saturated aqueous sodium chloride solution. The mixture was then dried over sodium sulfate, and was evaporated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (silica gel: 20 g, CHCl3 and CHCl3 /CH3OH (30:1)) to obtain 1.72 g (yield: 92%) of the subject compound as a pale yellow crystalline product.

Workup

  1. additionwas dropwise added over a period of 5-10 min.
  2. additionAfter the addition
  3. additionAfter the addition
  4. stirringthe mixture was stirred overnight at room temperature
  5. filtrationPrecipitated insolubles were filtered off
  6. washthe insolubles were washed with ethyl acetate
  7. washwashed twice with a saturated aqueous sodium hydrogencarbonate solution and once with a saturated aqueous sodium chloride solution
  8. dry with materialThe mixture was then dried over sodium sulfate
  9. customwas evaporated under reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by silica gel column chromatography (silica gel: 20 g, CHCl3 and CHCl3 /CH3OH (30:1))

Sources & evidence

ORD record
ord-b6582c129ab041b0b74a285983ca023a
Source dataset
uspto-grants-1988_08
Patent number
US04764617

Reaction notes

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