3-[2-(Pyrrolidin-1-yl)ethyl]aniline → HCID 178518316, compound

HRID 2236593Notes

Reaction equation

HRID 2236593 reaction equation
CO[CH:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[NH:6][C:5]1=[O:15].[N:16]1([CH2:21][CH2:22][C:23]2[CH:24]=[C:25]([NH2:29])[CH:26]=[CH:27][CH:28]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1>CN(C)C=O>[N:16]1([CH2:21][CH2:22][C:23]2[CH:24]=[C:25]([NH:29]/[CH:3]=[C:4]3\[C:5](=[O:15])[NH:6][C:7](=[O:14])[C:8]4[C:13]\3=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH:26]=[CH:27][CH:28]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 219550223-[2-(Pyrrolidin-1-yl)ethyl]anilineHCID 686923374-Methoxymethylene-4H-isoquinoline-1,3-dione

Product 1

HCID 178518316HCID 178518316, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared from a solution of 0.256 g (1.26 mmol) of 4-methoxymethylene-4H-isoquinoline-1,3-dione and 0.240 g (1.26 mmol) of 3-(2-pyrrolidin-1-yl-ethyl)-phenylamine in 4 mL of N,N-dimethylformamide (DMF) at 100° C. under N2 as described for example 21. After heating for 1 h, solvent is removed and the residue is filtered through Magnesol (20% MeOH in CHCl3). Solvent evaporation gave 0.420 g (92%) of a red glass: 1H NMR (DMSO-d6) δ 12.40 (d, 1H, J=9.0 Hz), 11.33 (s, 1H), 8.90 (d, 1H, J=9.0 Hz), 8.17 (d, 1H, J=6.0 Hz), 8.03 (d, 1H, J=6.0 Hz), 7.62 (m, 1H), 7.46 (s, 1H), 7.30 (m, 3H), 7.04 (d, 1H, J=6.0 Hz), 2.70 (m, 4H), 2.50 (m, 4H), 1.67 (m, 4H); HRMS (ESI) m/z calcd for C22H23N3O2 362.18631. found 362.18574 (M+H)−1; Analysis for C22H23N3O2.0.75H2O; Calcd: C, 70.46; H, 6.60; N, 11.21. Found: C, 70.83; 6.61; N, 11.24.

Workup

  1. temperatureAfter heating for 1 h
  2. customsolvent is removed
  3. filtrationthe residue is filtered through Magnesol (20% MeOH in CHCl3)
  4. customSolvent evaporation

Sources & evidence

ORD record
ord-eb1353fb8b744c728cb3af5b01995819
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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