Acetyl chloride → 1-[3-(4-Bromophenyl)pyrrolidin-1-yl]ethanone

HRID 1054603Notes

Reaction equation

HRID 1054603 reaction equation
C(N(CC)CC)C.Cl.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)=[CH:12][CH:11]=1.[C:21](Cl)(=[O:23])[CH3:22]>C1COCC1.O>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[CH2:20][CH2:19][N:18]([C:21](=[O:23])[CH3:22])[CH2:17]2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 534077083-(4-Bromophenyl)pyrrolidine hydrochloride

Product 1

HCID 842041851-[3-(4-Bromophenyl)pyrrolidin-1-yl]ethanoneYield 117.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (192 mg, 1.9 mmol) was added to a suspension of 3-(4-bromophenyl)pyrrolidine hydrochloride (200 mg, 0.76 mmol) in anhydrous THF (5 mL). The mixture was stirred at room temperature for 5 minutes and then treated with acetyl chloride (66 mg, 0.84 mmol). The reaction mixture was stirred for 20 hours at room temperature. The reaction mixture was diluted with water and extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give 1-[3-(4-bromophenyl)pyrrolidin-1-yl]ethanone (0.24 g, quantitative yield) as an oil which was used directly in the next step. MS (ES+) 267.9 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred for 20 hours at room temperature
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8eb867e16a9d414592188ed83c7b47b6
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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