Tetrahydrofuran → cis-4-amino-N-[1-(2-aminoethyl)-3-methoxy-4-piperidinyl]-5-chloro-2,3-dihydro-7-benzofurancarboxamide

HRID 742107ノート

反応式

HRID 742107 の反応式
[NH2:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([C:11]([NH:13][C@H:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]#[N:22])[CH2:16][C@H:15]2[O:23][CH3:24])=[O:12])=[CH:4][C:3]=1[Cl:25].O1CCCC1.[H][H]>[Ni].CO>[NH2:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([C:11]([NH:13][C@H:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][NH2:22])[CH2:16][C@H:15]2[O:23][CH3:24])=[O:12])=[CH:4][C:3]=1[Cl:25]

参加物

6

反応物 3

HCID 8028TetrahydrofuranHCID 86748327cis-4-amino-5-chloro-N-[1-(cyanomethyl)-3-methoxy-4-piperidinyl]-2,3-dihydro-7-benzofurancarboxamideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 67704537cis-4-amino-N-[1-(2-aminoethyl)-3-methoxy-4-piperidinyl]-5-chloro-2,3-dihydro-7-benzofurancarboxamide収率 53.6%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 887Methanol溶媒

実験手順

A solution of 15.7 parts of cis-4-amino-5-chloro-N-[1-(cyanomethyl)-3-methoxy-4-piperidinyl]-2,3-dihydro-7-benzofurancarboxamide in 178 parts of tetrahydrofuran and 158 parts of methanol was hydrogenated at normal pressure and at room temperature with 6 parts of Raney nickel. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH(NH3) 93:7). The eluent of the desired fraction was evaporated and the residue was crystallized from acetonitrile (to which a few drops of water were added). The product was filtered off at 0° C. and dried in vacuo at 40° C., yielding 8.5 parts (53.6%) of cis-4-amino-N-[1-(2-aminoethyl)-3-methoxy-4-piperidinyl]-5-chloro-2,3-dihydro-7-benzofurancarboxamide (comp. 35).

後処理

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH(NH3) 93:7)
  4. customThe eluent of the desired fraction was evaporated
  5. customthe residue was crystallized from acetonitrile (to which a few drops of water were added)
  6. filtrationThe product was filtered off at 0° C.
  7. customdried in vacuo at 40° C.

出典と根拠

ORDレコード
ord-01c9693be60146c18921b92cc5e52cbc
出典データセット
uspto-grants-1996_09
特許番号
US05552553

反応ノート

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