Water → 1-Benzoyl-3-[1-(4-isopropylbenzyl)piperid-4-yl]urea

HRID 3887

Reaction equation

HRID 3887 reaction equation
[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:12]([NH:20][C:21](=[O:29])[NH:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.O>CN(C)C=O>[C:12]([NH:20][C:21]([NH:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:8][C:7]2[CH:10]=[CH:11][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=2)[CH2:25][CH2:24]1)=[O:29])(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 749164-Isopropylbenzyl chlorideHCID 126085824-Benzoylureidopiperidine

Product 1

HCID 129423021-Benzoyl-3-[1-(4-isopropylbenzyl)piperid-4-yl]urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Isopropylbenzyl chloride (0.84 g, 0.005 m), 4-benzoylureidopiperidine (1.28 g, 0.005 m) and triethylamine (0.6 g) in dimethylformamide (25 cm3) were stirred at room temperature for 24 hours. Water was added and the precipitated solid filtered off. The solid was suspended in isopropylalcohol and acidified with ethanolic HCl. The title compound was filtered off and dried (1.2 g), m.p. 240°-242° C. as the hydrochloride salt, hemihydrate.

Workup

  1. filtrationthe precipitated solid filtered off
  2. filtrationThe title compound was filtered off
  3. dry with materialdried (1.2 g), m.p. 240°-242° C. as the hydrochloride salt, hemihydrate

Sources & evidence

ORD record
ord-35a5faba84b5422a9a52f12017701c29
Source dataset
uspto-grants-1988_02
Patent number
US04722930

Linked notes

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