Ammonium Chloride → 1-[5-(2-Bromophenyl)-1,5-dioxopentyl]pyrrolidine

HRID 1073645Notes

Reaction equation

HRID 1073645 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](=[O:21])[CH2:14][CH2:15][CH2:16][C:17](OC)=[O:18].[NH4+].[Cl-]>>[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](=[O:21])[CH2:14][CH2:15][CH2:16][C:17]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:18]

Participants

4

Reactant 3

HCID 25517Ammonium Chloride2×HCID 31268Pyrrolidine2×HCID 14582851Methyl 2-bromo-delta-oxobenzenepentanoate

Product 1

HCID 150876271-[5-(2-Bromophenyl)-1,5-dioxopentyl]pyrrolidine

Procedure

To 1 ml of pyrrolidine is added with stirring 0.100 g (0.35 mmol) of the product of Example 3, and 5 mg of NH4Cl. The combined reagents were stirred in a sealed tube for 16 hours at room temperature. After this time, an additional 1 ml of pyrrolidine and 5 mg of NH4Cl was added and the reaction mixture was stirred an additional 16 hours. The solvent was removed under reduced pressure and the residue was flash chromatographed. Elution with diethyl ether produced 0.13 g of the titled product, which was used without further purification.

Workup

  1. stirringthe reaction mixture was stirred an additional 16 hours
  2. customThe solvent was removed under reduced pressure
  3. customchromatographed
  4. washElution with diethyl ether

Sources & evidence

ORD record
ord-4bacad5adc7c4d36b4604b6f4117a866
Source dataset
uspto-grants-1990_11
Patent number
US04970234

Reaction notes

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