Triethylamine → methyl 4-[(hexahydro-1H-1,4-diazepin-1-yl)methyl]benzoate

HRID 16470

반응식

HRID 16470 반응식
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[N:1]1([CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 68163Hexahydro-1,4-diazepineHCID 256687Methyl 4-(bromomethyl)benzoateHCID 516892Sodium Bicarbonate

생성물 1

HCID 28881272methyl 4-[(hexahydro-1H-1,4-diazepin-1-yl)methyl]benzoate수율 56.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Alternatively, a mixture of hexahydro-1H-1,4-diazepine (17.47 g, 174.4 mmol) and methyl 4-(bromomethyl)benzoate (5.0 g, 21.8 mmol) was heated with triethylamine (24 mL, 174.4 mmol) in tetrahydrofuran (872 mL) to reflux for three hours. After cooling, the mixture was treated with saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Flash chromatography gave 3.04 g of methyl 4-[(hexahydro-1H-1,4-diazepin-1-yl)methyl]benzoate, 1H NMR (300 MHz, CDCl3) δ 7.98 (d, 2H), 7.42 (d, 2H), 3.90 (s, 3H), 3.70 (s, 2H), 2.97 (m, 2H), 2.91 (m, 2H), 2.67 (m, 2H), 2.66 (m, 2H), 1.77 (m, 2H).

후처리

  1. temperatureto reflux for three hours
  2. temperatureAfter cooling
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e2ad19f2a9f6489ab15b36cf06dd7004
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737145B2

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