Isopropylamine → 1-[1-(4-Fluorophenethyl)-piperdin-4-yl]-6-(isopropylcarbamoylmethyl)indoline

HRID 1790459Notes

Reaction equation

HRID 1790459 reaction equation
C(N1C=CN=C1)(N1C=CN=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]([OH:38])=O)[CH:33]=4)[CH2:28][CH2:27]3)[CH2:22][CH2:21]2)=[CH:16][CH:15]=1.[CH:41]([NH2:44])([CH3:43])[CH3:42].C(OCC)(=O)C>CN(C)C=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:38])[NH:44][CH:41]([CH3:43])[CH3:42])[CH:33]=4)[CH2:28][CH2:27]3)[CH2:22][CH2:21]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 220380431-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-carboxymethylindoline

Product 1

HCID 220379741-[1-(4-Fluorophenethyl)-piperdin-4-yl]-6-(isopropylcarbamoylmethyl)indolineYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under ice cooling, 1,1′-carbonyldimidazole (15 g) was added to a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-carboxymethylindoline (30 g) in dimethylformamide (240 ml) and the resultant mixture was stirred for 2 hr. After adding isopropylamine (5.6 g), the mixture was warmed to room temperature and then stirred for additional 2 hr. Next, ice water (240 ml) and ethyl acetate (300 ml) were added to the reaction solution and the layers were separated. The organic layer was washed successively with water, a saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in hot ethyl acetate (80 ml). After allowing to cool to room temperature, the resulting crystals were collected by filtration to give the title compound (17.2 g) as a white powder (yield: 52%).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed successively with water
  3. dry with materiala saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in hot ethyl acetate (80 ml)
  6. temperatureto cool to room temperature
  7. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-1cb140fd327d45739df3badf916eff95
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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