Dimethylformamide → 6-(4-Hydroxypiperidino)carbostyril

HRID 1085468Notes

Reaction equation

HRID 1085468 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.[OH:13][CH:14]([CH2:18][CH2:19]Br)[CH2:15][CH2:16]Br.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[OH:13][CH:14]1[CH2:18][CH2:19][N:1]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]3)[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 128107976-Aminoquinolin-2-olHCID 146275883-Hydroxy-1,5-dibromopentane

Product 1

HCID 104669946-(4-Hydroxypiperidino)carbostyril

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-aminocarbostyril, 1.6 g (0.01 mole), crude bromopentanes from step c, 3.1 g, anhydrous sodium carbonate, 2.0 g (0.020 mole), and dimethylformamide, 15 mL, was heated for 4.5 hours at 100° C. with occasional stirring. The mixture was then cooled and diluted with water, 150 mL, to give a pasty precipitate which was filtered off and washed with water to give a sticky solid (2.9 g). The solid was taken up in hot methanol and the insoluble material filtered off (0.6 g, mp 270°-280° C.). Further treatment with hot methanol gave 0.4 g of the desired product, mp 280°-283° C.

Workup

  1. temperatureThe mixture was then cooled
  2. customto give a pasty precipitate which
  3. filtrationwas filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-aa3186443b61459abdaf020318ca1b8f
Source dataset
uspto-grants-1991_04
Patent number
US05010088

Reaction notes

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