4-(Piperidin-1-ylmethyl)aniline → HCID 178487200, compound

HRID 2236612Notes

Reaction equation

HRID 2236612 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][C:7](=[O:14])/[C:6]/2=[CH:15]/OC.[N:18]1([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][C:7](=[O:14])[C:6]2=[CH:15][NH:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 8461504-(Piperidin-1-ylmethyl)anilineHCID 59299827(4E)-6-methoxy-4-methoxymethylene-4H-isoquinoline-1,3-dione

Product 1

HCID 178487200HCID 178487200, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (4E)-6-methoxy-4-methoxymethylene-4H-isoquinoline-1,3-dione (117 mg, 0.50 mmole), N,N-dimethylformamide (1 mL) and 4-piperidin-1-ylmethyl-phenylamine (95 mg, 0.50 mmole) is stirred and heated at 110° C. for one hour, cooled in the refrigerator overnight. The reaction mixture is evaporated to dryness, taken up in 7.5% methanol in chloroform and passed through a short pad of Florisil eluting with 7.5% methanol in chloroform. The eluate is evaporated in vacuo, treated with acetonitrile, filtered and dried to give a yellow solid 152 mg (78%), mp 272-5° C. dec; MS (ESI): m/z 392.4 (M+H).

Workup

  1. temperaturecooled in the refrigerator overnight
  2. customThe reaction mixture is evaporated to dryness
  3. customThe eluate is evaporated in vacuo
  4. additiontreated with acetonitrile
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-c51f6884faf54bb88ab5262fe55f2197
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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