4-(Piperidin-1-ylmethyl)aniline → HCID 178486407, compound

HRID 2236716Notes

Reaction equation

HRID 2236716 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[NH:7][C:6](=[O:15])/[C:5]/2=[CH:16]/OC.[N:19]1([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[NH:7][C:6](=[O:15])[C:5]2=[CH:16][NH:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 8461504-(Piperidin-1-ylmethyl)anilineHCID 59300399(4E)-6-bromo-7-methoxy-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178486407HCID 178486407, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (4E)-6-bromo-7-methoxy-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (156 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. The reaction mixture is evaporated to dryness, taken up in 5% methanol in chloroform and passed through a short pad of Florisil eluting with 5% methanol in chloroform. The eluate is evaporated in vacuo, treated with acetonitrile, filtered and dried to give a dull yellow solid 134 mg (57%), mp 264-7° C.; MS (ESI): m/z 470.1 (M+H).

Workup

  1. temperaturecooled in the refrigerator
  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-688eb637c8ab450099b4d58e117015af
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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