Water → 2-(4-Hydroxypiperidino)-4-(3,4-methylenedioxybenzyl)amino-6-cyanoquinazoline

HRID 1900680Notes

Reaction equation

HRID 1900680 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]#[N:24])[CH:8]=2)[N:3]=1.[OH:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.CN(C)C=O.O>C(OCC)(=O)C>[OH:25][CH:26]1[CH2:31][CH2:30][N:29]([C:2]2[N:11]=[C:10]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]4[O:20][CH2:21][O:22][C:16]=4[CH:15]=3)[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:23]#[N:24])[CH:8]=3)[N:3]=2)[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 79341Piperidin-4-olHCID 211839842-Chloro-4-(3,4-methylenedioxybenzyl)amino-6-cyanoquinazoline

Product 1

HCID 211839852-(4-Hydroxypiperidino)-4-(3,4-methylenedioxybenzyl)amino-6-cyanoquinazolineYield 35.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture comprising 339 mg of 2-chloro-4-(3,4-methylenedioxybenzyl)amino-6-cyanoquinazoline, 500 mg of 4-hydroxypiperidine and 20 ml of N,N-dimethylformamide was heated under reflux for 5 hours and poured into 50 ml of water, followed by the addition of 50 ml of ethyl acetate. The obtained mixture was filtered to remove insolubles. The organic layer of the filtrate was dried over magnesium sulfate and concentrated under a reduced pressure to give a crystalline residue. This residue was washed with chloroform to give 145 mg of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. filtrationThe obtained mixture was filtered
  4. customto remove insolubles
  5. dry with materialThe organic layer of the filtrate was dried over magnesium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customto give a crystalline residue
  8. washThis residue was washed with chloroform

Sources & evidence

ORD record
ord-bb9c7a4276a34320a7d4db9437819820
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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