Water → N-(((1-(2-Naphthalenylmethyl)-4-piperidinyl)amino)carbonyl)benzamide

HRID 703848

Reaction equation

HRID 703848 reaction equation
[C:1]([NH:9][C:10](=[O:18])[NH:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1.C(N(CC)CC)C.O>CN(C)C=O>[C:1]([NH:9][C:10]([NH:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[CH2:16][CH2:17]1)=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 703202-BromomethylnaphthaleneHCID 126085824-Benzoylureidopiperidine

Product 1

HCID 72002N-(((1-(2-Naphthalenylmethyl)-4-piperidinyl)amino)carbonyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Benzoylureidopiperidine (1.28 g, 0.005 m), 2-(bromomethyl)naphthalene (1.1 g, 0.005 m) and triethylamine (0.6 g, 0.006 m) in dimethylformamide (25 cm3) were stirred at room temperature for 23 hours. Water was added and the precipitated solid filtered off and washed well with water. The solid was suspended in warm ethanol, acidified with ethanolic HCl and then heated until all the solid had dissolved. The title compound crystallised and was collected as the hydrochloride salt, hemihydrate (1.6 g), m.p. 232°-234° C.

Workup

  1. filtrationthe precipitated solid filtered off
  2. washwashed well with water
  3. temperatureheated until all the solid
  4. dissolutionhad dissolved
  5. customThe title compound crystallised
  6. customwas collected as the hydrochloride salt, hemihydrate (1.6 g), m.p. 232°-234° C.

Sources & evidence

ORD record
ord-2444ffcef79640878ab08e7fdee2b5e2
Source dataset
uspto-grants-1991_01
Patent number
US04985438

Linked notes

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