Chloroacetyl chloride → 2-chloro-N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acetamide

HRID 643260노트

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HRID 643260 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:16][C:15]3([CH3:18])[CH2:17][CH:11]2[CH2:12][C:13]([CH3:20])([CH3:19])[CH2:14]3)=[O:9])=[CH:4][CH:3]=1.[Cl:21][CH2:22][C:23](Cl)=[O:24]>C1COCC1>[Cl:21][CH2:22][C:23]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]2[CH2:16][C:15]3([CH3:18])[CH2:17][CH:11]2[CH2:12][C:13]([CH3:20])([CH3:19])[CH2:14]3)=[O:9])=[CH:6][CH:7]=1)=[O:24]

참가 물질

4

반응물 2

HCID 6577Chloroacetyl chlorideHCID 577868(4-Amino-phenyl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone

생성물 1

HCID 684296572-chloro-N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acetamide수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (4-amino-phenyl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone (3.0 g, 11.01 mmol) and TEA (3.1 ml, 22.03 mmol) in dry THF (100 ml) was added dropwise chloroacetyl chloride (1.05 ml, 13.22 mmol). The mixture was stirred for 75 min. and evaporated followed by addition of water 75 (ml). The aqueous phase was extracted with EtOAc (2×50 ml) and the combined organic phases were dried (Na2SO4), filtered and evaporated in vacuo. The resulting residue was dissolved in EtOAc (40 ml) and filtered through a 2.5 cm path of silicagel. The filtrated was evaporated to dryness affording 3.3 g (86%) of 2-chloro-N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acetamide as an oil.

후처리

  1. customevaporated
  2. additionfollowed by addition of water 75 (ml)
  3. extractionThe aqueous phase was extracted with EtOAc (2×50 ml)
  4. dry with materialthe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. dissolutionThe resulting residue was dissolved in EtOAc (40 ml)
  8. filtrationfiltered through a 2.5 cm path of silicagel
  9. customThe filtrated was evaporated to dryness

출처 및 근거

ORD 기록
ord-41a1f22999314d96ac7d3e232eec7c2b
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700583B2

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