Hydrochloric Acid → HCID 19870590, compound

HRID 330162Notes

Reaction equation

HRID 330162 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12]([OH:14])=O)[CH:8]=2)[C:3](/[CH:15]=[CH:16]/[C:17]([OH:19])=O)=[CH:2]1.Cl.CN(C)[CH2:23][CH2:24][CH2:25][N:26]=[C:27]=NCC.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.Cl>CN(C)C1C=CN=CC=1.CN(C)C=O>[O:19]=[C:17]([N:26]1[CH2:25][CH2:24][CH2:23][CH2:27]1)/[CH:16]=[CH:15]/[C:3]1[C:4]2[C:9](=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[O:14])=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19870549HCID 19870549, compound

Product 1

HCID 19870590HCID 19870590, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of E,E-indole-3,6-diacrylic acid (1 g), 4-dimethylaminopyridine (1.19 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.86 g) and pyrrolidine (0.69 g) was dissolved in N,N-dimethylformamide (35 ml), and stirred under an atmosphere of nitrogen. Additional portions (10% by weight) of each of the reagents were added at the end of each 24 hour period (five times) until TLC monitoring indicated completion of the reaction after 6 days. The mixture was added slowly to vigorously-stirred 2M hydrochloric acid (100 ml); the precipitate was isolated by filtration, washed with water and dried under vacuum to give E,E-3,6-di(3-oxo-3-pyrrolidino-1-propenyl)indole (0.98 g, 69%) as a yellow powder; mp 268°-270° C.; partial NMR (250 MHz, DMSO-d6): 1.70°-2.02 (m, 8H, pyrrolidino H), 3.41(m, 4H, pyrrolidino H), 3.66(m, 4H, pyrrolidino H); 6.75(d, J=15.6 Hz, 1H, olefinic H); 6.94(d, J=15.5 Hz, 1H, olefinic H); 11.76(br s, 1H, NH-indole).

Workup

  1. additionAdditional portions (10% by weight) of each of the reagents were added at the end of each 24 hour period (five times) until TLC monitoring
  2. customcompletion of the reaction after 6 days
  3. additionThe mixture was added slowly
  4. customthe precipitate was isolated by filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-01d7af90ed0348bc94b9db66fe5dba7c
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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