Benzyl Bromide → N-(2-aminoethyl)-N-benzylpyridin-2-amine

HRID 464352노트

반응식

HRID 464352 반응식
C1(N(CCCN2C(=O)[C:20]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=O)C2C=CC=CN=2)C=CC=CC=1.[H-].[Na+].[NH2:30][CH2:31][CH2:32][NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1.[H][H].C(Br)C1C=CC=CC=1>CS(C)=O.O>[NH2:30][CH2:31][CH2:32][N:33]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)[CH2:18][C:19]1[CH:20]=[CH:23][CH:24]=[CH:25][CH:26]=1

참가 물질

8

반응물 5

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamineHCID 20186606N-[3-(N-phenyl-N-pyrid-2-ylamino)propyl]phthalimideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 19831051N-(2-aminoethyl)-N-benzylpyridin-2-amine

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
85 °C

실험 절차

2-Bromopyridine (15.8 g), ethylene diamine (30 g) and pyridine (10 ml) were heated together under reflux for 3 hr. The mixture was stripped to remove the excess of ethylene diamine and the residue taken up in water. The pH was adjusted to 14 and extracted with chloroform. The extracts were dried (K2CO3), stripped and the residue distilled at reduced pressure to give 2-(2-aminoethylamino) pyridine, 8.24 g (60%) bp 80° C., 0.01 mm Hg. (ii) A mixture of sodium hydride (0.53 g) and 2-(aminoethylamino)pyridine (2.74 g) in DMSO (30 ml) was heated slowly to 85° C. under nitrogen. After the evolution of hydrogen had ceased the solution was cooled to room temperature and benzyl bromide (2.37 ml) added dropwise keeping the temperature below 30° C. After a further 1 hr, water (200 ml) was added, the mixture extracted with ether and the extract washed with 2N hydrochloric acid. The pH of the aqueous layer was adjusted to 4.5 and extracted with chloroform. The pH was further raised to 14 and extracted with ether. After drying (K2CO3) and stripping, the final ether extract gave 2-[N-(2-aminoethyl)-N-benzylamino]pyridine (2.58 g) as an oil which was used without further purification.

후처리

  1. temperaturewas cooled to room temperature
  2. customthe temperature below 30° C
  3. extractionthe mixture extracted with ether
  4. washthe extract washed with 2N hydrochloric acid
  5. extractionextracted with chloroform
  6. temperatureThe pH was further raised to 14
  7. extractionextracted with ether
  8. dry with materialAfter drying (K2CO3)
  9. extractionthe final ether extract

출처 및 근거

ORD 기록
ord-6f7667e4876046e9907c71d1adbf4efa
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04547506

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