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 325703ノート

反応式

HRID 325703 の反応式
[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

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 127501,2,3,6-TetrahydropyridineHCID 4311764Sodium borohydrideHCID 178486227HCID 178486227、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4565f40f93e94c3da37c34bc3d608039
出典データセット
uspto-grants-1984_04
特許番号
US04442110

反応ノート

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