Diethyl Ether → HCID 178518342, compound

HRID 2236607Notes

Reaction equation

[I: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([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(OCC)C>CN(C=O)C>[I: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:26]=[CH:25][C:24]([CH2:23][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 0.2 g (0.60 mmol) of (4E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione in 2 mL of N,N′-dimethylformamide is added 4-piperidin-1-ylmethyl-phenylamine (0.127 mL, 0.67 mmol). The reaction mixture is heated at 120° C. under N2 for 1.5 h. After cooling, ethyl ether is added and left in refrigerator overnight to give dark brown crystal. The crystal is collected and dissolved in 4 mL of dimethyl sulfoxide, followed by addition of 6 mL of 65% MeOH/H2O solution to give a precipitate. The solid is collected and washed thoroughly with water, MeOH, Et2O and hexane, and air-dried to give 0.143 g (48.3% yield) of tan solid: mp 202-203° C., MS (ESI) m/z 488.1 (M+H)+1

Workup

temperatureAfter cooling
customto give dark brown crystal
customThe crystal is collected
dissolutiondissolved in 4 mL of dimethyl sulfoxide
additionfollowed by addition of 6 mL of 65% MeOH/H2O solution
customto give a precipitate
customThe solid is collected
washwashed thoroughly with water, MeOH, Et2O and hexane
customair-dried

Sources & evidence

ORD record: ord-dff823a76ecb49788420b38a3a3a8fa5
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713994B2

Reaction notes

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