Water → 1-Benzoyl-3-[1-(2-[1,4-benzodioxan-2-yl]-2-oxoethyl)piperid-4-yl]-urea

HRID 225143Notes

Reaction equation

HRID 225143 reaction equation
[C:1]([NH:9][C:10]([NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:20][C:21]([CH:23]1[O:28][C:27]2[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=2[O:25][CH2:24]1)=[O:22].C(N(CC)CC)C.O>CN(C)C=O>[C:1]([NH:9][C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:20][C:21]([CH:23]2[O:28][C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[O:25][CH2:24]2)=[O:22])[CH2:15][CH2:14]1)=[O:11])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 126085824-BenzoylureidopiperidineHCID 126085852-Bromo-1-(2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-one

Product 1

HCID 126085861-Benzoyl-3-[1-(2-[1,4-benzodioxan-2-yl]-2-oxoethyl)piperid-4-yl]-ureaYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Benzoyl-3-(piperid-4-yl)urea (2.46 g, 0.01 mol) and 2-bromoacetyl-1,4-benzodioxan (2.57 g, 0.01 mol) in dry dimethylformamide (40 mls) were stirred at room temperature. Triethylamine (1,1 g, 1.5 cm3) was added and the suspension stirred for 1 hour. Water was added and the solid filtered off (4.20 g, 100%). The solid was suspended in methanol (40 mls) and ethanolic hydrogen chloride added until the solution was acidic. The title compound was filtered off as the hydrochloride salt and dried (yield 3.51 gm 76% yield). Melting pt. 160°-161° C.

Workup

  1. filtrationthe solid filtered off (4.20 g, 100%)
  2. additionethanolic hydrogen chloride added until the solution
  3. filtrationThe title compound was filtered off as the hydrochloride salt
  4. customdried (yield 3.51 gm 76% yield)

Sources & evidence

ORD record
ord-7223e09ddead4acba80c669284a9b226
Source dataset
uspto-grants-1980_11
Patent number
US04235915

Reaction notes

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