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

HRID 327387노트

반응식

HRID 327387 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f4aa843298184aa585394698f9d79ee3
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05273972

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