Water → 6-{[4-Hydroxy-4-(3-methoxyphenyl)-1-piperidinyl]acetyl}-3,4-dihydroquinolin-2(1h)-one

HRID 50854Notes

Reaction equation

HRID 50854 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)=[O:4].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:24]2([OH:30])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:21]=[CH:22][CH:23]=1.C(N(CC)CC)C.O>CN(C=O)C>[OH:30][C:24]1([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH3:16])[CH:19]=2)[CH2:25][CH2:26][N:27]([CH2:2][C:3]([C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]3)=[O:4])[CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10910764-(3-Methoxyphenyl)piperidin-4-olHCID 49617906-(2-Chloroacetyl)-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 227369406-{[4-Hydroxy-4-(3-methoxyphenyl)-1-piperidinyl]acetyl}-3,4-dihydroquinolin-2(1h)-oneYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-(Chloroacetyl)-3,4-dihydroquinolin-2(1H)-one (7.30 g, 32.7 mmol) in DMF (32 ml) were added 4-(3-methoxyphenyl)-4-piperidinol (J. Labelled Compd. Radiopharm., 41, p464, 1998). (8.12 g, 39.2 mmol) and triethylamine (13.7 ml, 98.0 mmol) at room temperature under nitrogen. The reaction mixture was stirred for 4 hours at room temperature and poured into water (80 ml). The precipitate was collected by filtration and washed with dichloromethane (20 ml). The solid was stirred in 0.5N NaOH (65 ml) for 1 hour at room temperature and the suspension was filtered to afford the title compound (5.98 g, 46%) as a yellow solid.

Workup

  1. customat room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with dichloromethane (20 ml)
  4. stirringThe solid was stirred in 0.5N NaOH (65 ml) for 1 hour at room temperature
  5. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-d86044666d9546f3a6c6ddc2f0319d7b
Source dataset
uspto-grants-2004_03
Patent number
US06713490B2

Reaction notes

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