4-(Pyrrolidin-1-ylmethyl)aniline → HCID 178518259, compound

HRID 2236645Notes

Reaction equation

HRID 2236645 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][C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=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:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 7768524-(Pyrrolidin-1-ylmethyl)anilineHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione

Product 1

HCID 178518259HCID 178518259, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

To a suspension of crude 6-Bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (56.4 mg, 0.2 mmol) in N,N-dimethylformamide (500 μL) is added 4-pyrrolidin-1-ylmethyl-phenylamine (35.2 mg, 0.2 mmol). The reaction mixture is shaken at 115° C. for 1.5 hours. Upon cooling to room temperature, the product precipitated out. The precipitate is then filtered off, rinsed with copious amounts of ether, and dried to yield 78.8 mg of 6-Bromo-4-[(4-pyrrolidin-1-ylmethyl-phenylamino)-methylene]-4H-isoquinoline-1,3-dione.

Workup

  1. temperatureUpon cooling to room temperature
  2. customthe product precipitated out
  3. filtrationThe precipitate is then filtered off
  4. washrinsed with copious amounts of ether
  5. customdried

Sources & evidence

ORD record
ord-5ab70e908e744f1fbd94e90d97d978c4
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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