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

HRID 734847

반응식

HRID 734847 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-59de8ca491d041b88695725a4313be7d
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592358B2

연결된 노트

불러오는 중…