Triethylamine → 1-(4-Bromophenethyl)pyrrolidine

HRID 2362671Notes

Reaction equation

HRID 2362671 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)(=O)=O)=CC=1.[CH2:21]([N:23](CC)[CH2:24][CH3:25])[CH3:22].N1CCCC1>C(#N)C.C(OCC)(=O)C>[Br:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][N:23]2[CH2:24][CH2:25][CH2:22][CH2:21]2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 14606696HCID 14606696, compound

Product 1

HCID 121778101-(4-Bromophenethyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-bromophenethyl 4-methylbenzenesulfonate (500 mg, 1.407 mmol) from Example 56A in anhydrous acetonitrile (3 mL) was treated with triethylamine (0.589 mL, 4.22 mmol) and pyrrolidine (0.349 mL, 4.22 mmol). The reaction was stirred 16 hours at ambient temperature. The reaction was diluted with ethyl acetate and washed with water, saturated ammonium chloride, and brine. The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 5% methanol in dichloromethane, to give the title compound. MS DCI(+) m/z 254.0 [M+H]+.

Workup

  1. washwashed with water, saturated ammonium chloride, and brine
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting with a gradient of 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-cdf5c03d4e6249099226031c74544f23
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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