Pyrrolidine → 4-(4-Pyrrolidin-1-ylcarbonylbenzyl)-nitrobenzene

HRID 634822Notes

Reaction equation

HRID 634822 reaction equation
Cl[C:2]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)=[O:3].[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>ClCCl.N1C=CC=CC=1>[N:20]1([C:2]([C:4]2[CH:19]=[CH:18][C:7]([CH2:8][C:9]3[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=3)=[CH:6][CH:5]=2)=[O:3])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 2584714-(4-Chlorocarbonylbenzyl)-nitrobenzene

Product 1

HCID 120943914-(4-Pyrrolidin-1-ylcarbonylbenzyl)-nitrobenzeneYield 99%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

4-(4-Chlorocarbonylbenzyl)-nitrobenzene was dissolved in dichloromethane (40 mL) and a solution of pyrrolidine (64 mg, 1 eq) in pyridine (0.2 mL) was added. The mixture was stirred for 2 hours at room temperature, washed with dilute potassium hydroxide, and solvents evaporated to yield a yellow oil. The residue was chromatographed on silica gel, eluting with dichloromethane/methanol, to give 4-(4-pyrrolidin-1-ylcarbonylbenzyl)-nitrobenzene (299 mg, 99%).

Workup

  1. washwashed with dilute potassium hydroxide, and solvents
  2. customevaporated
  3. customto yield a yellow oil
  4. customThe residue was chromatographed on silica gel
  5. washeluting with dichloromethane/methanol

Sources & evidence

ORD record
ord-fce7b51e61de4fe8a70b933780fc0081
Source dataset
uspto-grants-2001_02
Patent number
US06184242B2

Reaction notes

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