4-(2-(Pyrrolidin-1-yl)ethyl)aniline → HCID 178518318, compound

HRID 2236585Notes

Reaction equation

HRID 2236585 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:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=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]=[CH:25][C:26]([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:27][CH:28]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 64870474-(2-(Pyrrolidin-1-yl)ethyl)anilineHCID 686923374-Methoxymethylene-4H-isoquinoline-1,3-dione

Product 1

HCID 178518318HCID 178518318, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-methoxymethylene-4H-isoquinoline-1,3-dione (101.5 mg, 0.5 mmol), 4-(2-pyrrolidin-1-yl-ethyl)-phenylamine (95.2 mg, 0.5 mmol) in 1 mL of N,N-dimethylformamide is heated at 110° C. for 1.5 h. After cooling in the refrigerator, the precipitate is collected, and washed with ether to give 129 mg (71%) of yellow solid mp 224-225° C.; MS (ESI) m/z 362.20 (M+1); Analysis for C22H23N3O2: Calcd: C, 73.11; H, 6.41; N, 11.63. Found: C, 72.33; H, 6.45; N, 11.59.

Workup

  1. temperatureAfter cooling in the refrigerator
  2. customthe precipitate is collected
  3. washwashed with ether

Sources & evidence

ORD record
ord-59c62616a4f94dc9924864770cbbd414
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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