Hydrochloric Acid → 1-Methyl-N5-[3-[3-[1-(1,2,3,6-tetrahydropyridinyl)methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine

HRID 2058725노트

반응식

HRID 2058725 반응식
[C:1]([N:3]=[C:4]([N:21]([CH3:30])[N:22]=CC1C=CC=CC=1)[NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]2OCCO2)[CH:11]=1)#[N:2].Cl.[NH:32]1[CH2:37][CH:36]=[CH:35][CH2:34][CH2:33]1.[BH4-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:30][N:21]1[C:4]([NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][N:32]3[CH2:33][CH:34]=[CH:35][CH2:36][CH2:37]3)[CH:11]=2)=[N:3][C:1]([NH2:2])=[N:22]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 127501,2,3,6-TetrahydropyridineHCID 4311764Sodium borohydrideHCID 178486227HCID 178486227, 화합물

생성물 1

HCID 867382851-Methyl-N5-[3-[3-[1-(1,2,3,6-tetrahydropyridinyl)methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of N'-cyano-N-[3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl]-1-methyl-2-(phenylmethylene)hydrazinecarboximidamide (2.62 g) in tetrahydrofuran (40 ml) was stirred at room temperature for 0.5 h with 2 N hydrochloric acid (5 ml). The mixture was treated with 1,2,3,6-tetrahydropyridine (9 ml) and stirred at room temperature for a further 1 h. The mixture was treated with sodium borohydride (1.5 g), stirred at room temperature for 18 h, diluted with ethyl acetate, filtered and the filtrate evaporated in vacuo. The resulting oil was partitioned between ethyl acetate and water. The organic phase was evaporated in vacuo and the residue was purified by column chromatography on silica, using methanol. Evaporation of the eluates gave the title compound which was recrystallised from a mixture of benzene and cyclohexane (1.26 g) m.p. 102°-3°. TLC silica; methanol-ammonia 80:1; Rf 0.6.

후처리

  1. stirringstirred at room temperature for 18 h
  2. filtrationfiltered
  3. customthe filtrate evaporated in vacuo
  4. customThe resulting oil was partitioned between ethyl acetate and water
  5. customThe organic phase was evaporated in vacuo
  6. customthe residue was purified by column chromatography on silica
  7. customEvaporation of the eluates

출처 및 근거

ORD 기록
ord-f19f7ab1ebd84eebabd48552a189e0c8
출처 데이터셋
uspto-grants-1982_03
특허 번호
US04318913

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