Triethylamine → 1-[2-(4-Bromo-2-chloromethylphenoxy)ethyl]pyrrolidine

HRID 734847

Reaction equation

HRID 734847 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:7]=[CH:8][C:9]([O:14][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:10]([CH2:12]O)[CH:11]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([O:14][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:10]([CH2:12][Cl:3])[CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 211828631-[2-(2-Hydroxymethyl-4-bromophenoxy)ethyl]pyrrolidine

Product 1

HCID 690598221-[2-(4-Bromo-2-chloromethylphenoxy)ethyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.16 mL (2.20 mmol) of thionyl chloride was added at −10° C. to a solution of 0.60 g (2.00 mmol) of [5-bromo-2-(2-pyrrolidin-1-ylethoxy)phenyl]methanol and 0.42 mL (3.00 mmol) of triethylamine in 30 mL of THF and the mixture was stirred for 16 hours at RT. Ice and dilute aqueous sodium bicarbonate solution was added to the reaction mixture and the phases were separated. The aqueous phase was exhaustively extracted with DCM, and the combined organic phases were washed with water, dried over magnesium sulfate, and evaporated down in vacuo. Yield: 0.39 g (62% of theoretical); C13H17BrClNO (M=318.637); calc.: molpeak (M+H)+: 318/320/322 (BrCl); found: molpeak (M+H)+: 318/320/322 (BrCl); HPLC-MS: 5.84 minutes (method A).

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was exhaustively extracted with DCM
  3. washthe combined organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down in vacuo
  6. custom5.84 minutes (method A)

Sources & evidence

ORD record
ord-59de8ca491d041b88695725a4313be7d
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Linked notes

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