Triethylamine → N-Methyl-2-(4-methylpiperazin-1-yl)ethan-1-amine

HRID 1842763노트

반응식

HRID 1842763 반응식
C(Cl)(=O)O[CH2:3][CH3:4].[CH3:7][NH:8][CH2:9][CH2:10][N:11]1C[CH2:15][NH:14][CH2:13][CH2:12]1.C(N(CC)CC)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.O>[CH3:7][NH:8][CH2:9][CH2:10][N:11]1[CH2:4][CH2:3][N:14]([CH3:15])[CH2:13][CH2:12]1

참가 물질

9

반응물 6

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 17845519Methyl[2-(piperazin-1-YL)ethyl]amineHCID 21226445Aluminium lithium hydride

생성물 1

HCID 14979290N-Methyl-2-(4-methylpiperazin-1-yl)ethan-1-amine수율 55%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

Ethyl carbonochloridate (8.14 mL, 85.14 mmol) was added dropwise to N-methyl-2-piperazin-1-ylethanamine (5.0 g, 38.7 mmol) and triethylamine (12.95 mL, 92.88 mmol) in THF (40 mL) at 0° C. over a period of 10 minutes under N2. The resulting mixture was allowed to warm to r.t. and stirred for 2 h. The resulting white suspension was filtered, and washed through with THF (2×20 mL). The filtrate was concentrated in vacuo and the resulting residue was dissolved in EtOAc (75 mL). This solution was washed with sat. Na2CO3 (50 mL). The aqueous wash solution was then extracted with EtOAc (50 mL). The combined organic solutions were dried (MgSO4) and concentrated in vacuo to give crude intermediate (10.55 g). This was dissolved in THF (60 mL) and cooled to 0° C. LiAlH4 (101 mL, 100.6 mmol, 1M in THF) was added dropwise under N2. The resulting mixture was stirred at reflux overnight, then cooled to 0° C. and treated successively (dropwise) with water (3.8 mL), 15% aq. NaOH (3.8 mL) and water (11.4 mL) with rapid stirring. Diatomaceous earth (Celite™) and MgSO4 were added and the mixture was filtered, washed with EtOAc and the filtrate was concentrated in vacuo to give a colourless oil (3.35 g). The filtercake was washed with EtOAc (100 mL), heated to 70° C. and then filtered. The filtrate was concentrated in vacuo to give a further batch (1.023 g) of the title compound. Total: 4.37 g, 72%; 1H NMR: (CDCl3) 2.28 (3H, s), 2.33-2.6 (13H, m), 2.67 (2H, t).

후처리

  1. filtrationThe resulting white suspension was filtered
  2. washwashed through with THF (2×20 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionthe resulting residue was dissolved in EtOAc (75 mL)
  5. washThis solution was washed with sat. Na2CO3 (50 mL)
  6. extractionThe aqueous wash solution was then extracted with EtOAc (50 mL)
  7. dry with materialThe combined organic solutions were dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give crude intermediate (10.55 g)
  10. temperaturecooled to 0° C
  11. stirringThe resulting mixture was stirred
  12. temperatureat reflux overnight
  13. temperaturecooled to 0° C.
  14. filtrationthe mixture was filtered
  15. washwashed with EtOAc
  16. concentrationthe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-a638f696786b4e2cb444b26eea7733e0
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946235B2

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