Ethylamine hydrochloride → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(ethylcarbamoylmethyl)indoline

HRID 1790458Notes

Reaction equation

HRID 1790458 reaction equation
C(N1C=CN=C1)([N:3]1[CH:7]=[CH:6]N=C1)=O.[F:13][C:14]1[CH:40]=[CH:39][C:17]([CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[C:34]4[C:29](=[CH:30][CH:31]=[C:32]([CH2:35][C:36](O)=[O:37])[CH:33]=4)[CH2:28][CH2:27]3)[CH2:22][CH2:21]2)=[CH:16][CH:15]=1.Cl.C(N)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[F:13][C:14]1[CH:40]=[CH:39][C:17]([CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][CH:23]([N:26]3[C:34]4[C:29](=[CH:30][CH:31]=[C:32]([CH2:35][C:36](=[O:37])[NH:3][CH2:7][CH3:6])[CH:33]=4)[CH2:28][CH2:27]3)[CH2:24][CH2:25]2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 220380431-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-carboxymethylindoline

Product 1

HCID 220383431-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(ethylcarbamoylmethyl)indolineYield 60.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under ice cooling, 1,1′-carbonyldiimidazole (1.0 g) was added to a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-carboxymethylindoline (2.0 g) in dimethylformamide (40 ml). After stirring the mixture for 2 hr, ethylamine hydrochloride (0.51 g) was added thereto. Then the resultant mixture was allowed to warm to room temperature and stirred for additional 5 hr. A saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the reaction solution and the layers were separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Then the residue was dissolved in hot toluene (10 ml). After allowing to cool to room temperature, the resulting crystals were collected by filtration to give the title compound (1.3 g) as a white powder (yield: 56%).

Workup

  1. stirringstirred for additional 5 hr
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThen the residue was dissolved in hot toluene (10 ml)
  7. temperatureto cool to room temperature
  8. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-436e57e046c14b64a8417132af3d956e
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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