4-(2-(Pyrrolidin-1-yl)ethyl)aniline → HCID 178518257, compound

HRID 2236652Notes

Reaction equation

HRID 2236652 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14]OC.[N:17]1([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14][NH:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][CH2:22][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 64870474-(2-(Pyrrolidin-1-yl)ethyl)anilineHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione

Product 1

HCID 178518257HCID 178518257, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.300 g (1.06 mmol) of 6-bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione and 0.222 g (1.17 mmol) of 4-(2-pyrrolidin-1-yl-ethyl)-phenylamine in 1.8 mL of N,N-dimethylformamide (DMF) is heated at 120° C. for 1 h. The reaction is placed in a freezer and the precipitated material is collected, washed with cold N,N-dimethylformamide (DMF) (2×), cold MeOH (2×) and Et2O and dried in vacuo to give 0.307 g (66%) of brick red crystals: mp 212-214° C. (dec);

Workup

  1. customthe precipitated material is collected
  2. washwashed with cold N,N-dimethylformamide (DMF) (2×), cold MeOH (2×) and Et2O
  3. customdried in vacuo
  4. customto give 0.307 g (66%) of brick red crystals

Sources & evidence

ORD record
ord-9519d0a32fbb4c9b890768eb3ea0192a
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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