4-Nitrobenzyl chloride → HCID 54247637, compound

HRID 2288180Notes

Reaction equation

HRID 2288180 reaction equation
Cl.[F:2][C:3]([F:32])([F:31])[C:4]1[CH:5]=[C:6]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:7]([N:9]1[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)=[O:8].[N+:33]([C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Cl)=[CH:38][CH:37]=1)([O-:35])=[O:34].C(N(CC)CC)C>O1CCCC1>[F:30][C:27]([F:29])([F:28])[C:25]1[CH:24]=[C:6]([CH:5]=[C:4]([C:3]([F:2])([F:31])[F:32])[CH:26]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:40][C:39]2[CH:42]=[CH:43][C:36]([N+:33]([O-:35])=[O:34])=[CH:37][CH:38]=2)[CH2:11][C@H:10]1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)=[O:8]

Participants

5

Reactant 3

HCID 74824-Nitrobenzyl chlorideHCID 8471TriethylamineHCID 86584231HCID 86584231, compound

Product 1

HCID 54247637HCID 54247637, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dichlorobenzyl)piperazine hydrochloride (200 mg), 4-nitrobenzyl chloride (158 mg) and triethylamine (268 μl) in tetrahydrofuran (5 ml) was refluxed overnight. After cooling, the precipitates were filtered off and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of toluene and ethyl acetate as an eluent to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dichlorobenzyl)-4-(4-nitrobenzyl)piperazine (169.8 mg).

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. filtrationthe precipitates were filtered off
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel with a mixture of toluene and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-b558b75cc3174c10bb1022f345ce6e11
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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