1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → HCID 15257494, compound

HRID 2107641Notes

Reaction equation

HRID 2107641 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:2]1.Br[CH2:17][CH2:18][N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29].C(=O)([O-])O.[Na+]>CN(C)C=O>[C:20]1(=[O:29])[N:19]([CH2:18][CH2:17][N:13]2[CH2:14][CH2:15][CH:10]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)[CH2:11][CH2:12]2)[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]12

Participants

5

Reactant 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 516892Sodium BicarbonateHCID 7022353-(4-Piperidinyl)-1H-indole

Product 1

HCID 15257494HCID 15257494, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3-indolyl)piperidine (7.88 g), N-(2-bromoethyl)phthalimide (10.0 g) and sodium hydrogen carbonate (3.64 g) in dry N,N-dimethylformamide (93 ml) was heated at 68°-74° C. for 4 hours. After cooling, the reaction mixture was poured into ice-water (1,000 ml). The resulting precipitate was collected by filtration and washed with methanol to give 1-(2-phthalimidoethyl)-4-(3-indolyl)piperidine (5.53 g).

Workup

  1. temperaturewas heated at 68°-74° C. for 4 hours
  2. temperatureAfter cooling
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with methanol

Sources & evidence

ORD record
ord-888dfc5e9a834f2695f6387d3efc324f
Source dataset
uspto-grants-1990_06
Patent number
US04935432

Reaction notes

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