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

HRID 1284566Notes

Reaction equation

HRID 1284566 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-0cf3f0eb8c4c4f149dfd4dd387a006c3
Source dataset
uspto-grants-1986_01
Patent number
US04563466

Reaction notes

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