Acetonitrile → HCID 23135106, compound

HRID 254277Notes

Reaction equation

HRID 254277 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([CH:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)=[O:8].[OH:19][C:20]1[CH:21]=[C:22](N2CCNCC2)[CH:23]=[CH:24][CH:25]=1.C([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])C.CC#[N:41]>>[OH:19][C:20]1[CH:21]=[C:22]([CH:35]2[CH2:36][NH:41][CH2:38][CH2:37][N:34]2[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)=[O:8])[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 27365971-(3-Hydroxyphenyl)piperazineHCID 66852491HCID 66852491, compound

Product 1

HCID 23135106HCID 23135106, compoundYield 54%

Procedure

A mixture of the bromo adduct E1 (100 mg, 0.32 mmol), of commercial 3-hydroxyphenyl piperazine (57 mg, 0.32 mmol) and triethylamine (0.07 mL, 0.5 mmol) in CH3CN are reluxed during 16 h. The solvent is evaporated and the residue is taken up in CH2Cl2 (15 mL), washed with brine, dried and concentrated. The residue is purified by chromatography eluting with AcOEt:MeOH (9/1) to yield the titled adduct (mp 152° C., 70 mg, 54%)

Workup

  1. customThe solvent is evaporated
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue is purified by chromatography
  6. washeluting with AcOEt

Sources & evidence

ORD record
ord-d5c811394752484d9f35c8383a6030e7
Source dataset
uspto-grants-2011_01
Patent number
US07875617B2

Reaction notes

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