1,1'-Carbonyldiimidazole → 5-Chloro-2-methoxy-4-(methylamino)-N-[2-(1-piperidinyl-methyl)-1-azabicyclo[2.2.2]oct-3-yl]benzamide

HRID 327387ノート

反応式

HRID 327387 の反応式
[Cl:1][C:2]1[C:3]([NH:13][CH3:14])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[N:27]1([CH2:33][CH:34]2[CH:39]([NH2:40])[CH:38]3[CH2:41][CH2:42][N:35]2[CH2:36][CH2:37]3)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>O1CCCC1>[Cl:1][C:2]1[C:3]([NH:13][CH3:14])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([NH:40][CH:39]1[CH:38]2[CH2:37][CH2:36][N:35]([CH2:42][CH2:41]2)[CH:34]1[CH2:33][N:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1)=[O:9]

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 116942165-Chloro-2-methoxy-4-(methylamino)benzoic acidHCID 191084162-(1-Piperidylmethyl)-1-azabicyclo[2.2.2]octan-3-amine

生成物 1

HCID 98022695-Chloro-2-methoxy-4-(methylamino)-N-[2-(1-piperidinyl-methyl)-1-azabicyclo[2.2.2]oct-3-yl]benzamide収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 5-chloro-2-methoxy-4-(methylamino)-benzoic acid (1.95 g, 9.0 mmoles) in anhydrous tetrahydrofuran (10 ml) was treated with 1,1'-carbonyldiimidazole (1.49 g, 9.2 mmoles), stirred at room temperature for 90 minutes, then added to a cooled (0° C.) solution of 2-(1-piperidylmethyl)-1-azabicyclo[2.2.2]octan-3-amine (2.12 g, 9.5 mmoles) in anhydrous tetrahydrofuran (10 ml) under nitrogen. After 18 hours at room temperature the solution was concentrated in vacuo and partitioned between methylene chloride (100 ml) and 1.0N sodium hydroxide (40 ml). The organic solution was separated and washed with 1.0N sodium hydroxide (40 ml), saturated aqueous sodium bicarbonate (40 ml), and brine (40 ml), dried (Na2SO4), and concentrated in vacuo. Filtration through alumina (eluted with 15% methanol/ethyl acetate) provided 3.24 g (86%) of a colorless foam.

後処理

  1. additionadded to
  2. concentrationAfter 18 hours at room temperature the solution was concentrated in vacuo
  3. custompartitioned between methylene chloride (100 ml) and 1.0N sodium hydroxide (40 ml)
  4. customThe organic solution was separated
  5. washwashed with 1.0N sodium hydroxide (40 ml), saturated aqueous sodium bicarbonate (40 ml), and brine (40 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. filtrationFiltration through alumina (eluted with 15% methanol/ethyl acetate)

出典と根拠

ORDレコード
ord-f4aa843298184aa585394698f9d79ee3
出典データセット
uspto-grants-1993_12
特許番号
US05273972

反応ノート

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