4-(p-Tolyl)piperidin-4-ol → 1-[2-(4-Hydroxy-4-p-tolyl-piperidin-1-yl)-ethyl]-3-(2-methyl-quinolin-4-yl)-urea

HRID 2223708Notes

Reaction equation

HRID 2223708 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([C:7]2([OH:13])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.Cl[CH2:16][CH2:17][NH:18][C:19]([NH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[C:24]([CH3:32])[CH:23]=1)=[O:20].C([O-])(O)=O.[Na+].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>C1COCC1>[OH:13][C:7]1([C:4]2[CH:3]=[CH:2][C:1]([CH3:14])=[CH:6][CH:5]=2)[CH2:8][CH2:9][N:10]([CH2:16][CH2:17][NH:18][C:19]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[C:24]([CH3:32])[CH:23]=2)=[O:20])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 939124-(p-Tolyl)piperidin-4-olHCID 1859152-NaphthylalanineHCID 516892Sodium BicarbonateHCID 23443661-(2-Chloroethyl)-3-(2-methylquinolin-4-yl)urea

Product 1

HCID 179565681-[2-(4-Hydroxy-4-p-tolyl-piperidin-1-yl)-ethyl]-3-(2-methyl-quinolin-4-yl)-urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-p-tolyl-piperidin-4-ol (0.03 mmol) in dry THF (1 mL) is added 1-(2-chloro-ethyl)-3-(2-methyl-quinolin-4-yl)-urea (0.03 mmol), solid NaHCO3 (2.5 mg), and Nal (1 mg). The flask is tightly sealed, and shaken at 70° C. for 6 days. The reaction mixture is evaporated, taken up in aqueous formic acid, and purified by preparative HPLC to provide the title compound.

Workup

  1. customThe flask is tightly sealed
  2. customThe reaction mixture is evaporated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-5d955996203d47a9ae7fd01ecd32c7c1
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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