Water → 5-(3,4-Dichlorophenyl)-5-[2-[4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl]ethyl]-3-[3,5-bis(trifluoromethyl)benzyl]tetrahydro-2H-1,3-oxazin-2-one chloride

HRID 849340ノート

反応式

HRID 849340 の反応式
[C:1]1([C:7]23[CH2:14][CH2:13][N:10]([CH2:11][CH2:12]2)[CH2:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:15][C:16]([F:51])([F:50])[C:17]1[CH:18]=[C:19]([CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1)[CH2:20][N:21]1[CH2:26][C:25]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=2)([CH2:27][CH2:28]OS(C)(=O)=O)[CH2:24][O:23][C:22]1=[O:42].O.CCOCC>CN(C=O)C>[Cl-:40].[Cl:41][C:36]1[CH:35]=[C:34]([C:25]2([CH2:27][CH2:28][N+:10]34[CH2:13][CH2:14][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)([CH2:8][CH2:9]3)[CH2:12][CH2:11]4)[CH2:24][O:23][C:22](=[O:42])[N:21]([CH2:20][C:19]3[CH:18]=[C:17]([C:16]([F:51])([F:50])[F:15])[CH:45]=[C:44]([C:46]([F:49])([F:47])[F:48])[CH:43]=3)[CH2:26]2)[CH:39]=[CH:38][C:37]=1[Cl:40]

参加物

6

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 1428104-Phenyl-1-azabicyclo(2.2.2)octaneHCID 158866773-[3,5-Bis(trifluoromethyl)benzyl]-5-(3,4-dichlorophenyl)-5-[2-(methanesulfonyloxy)ethyl]tetrahydro-2H-1,3-oxazin-2-one

生成物 1

HCID 195913605-(3,4-Dichlorophenyl)-5-[2-[4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl]ethyl]-3-[3,5-bis(trifluoromethyl)benzyl]tetrahydro-2H-1,3-oxazin-2-one chloride収率 24.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of 0.53 g of 4-phenyl-1-azabicyclo-[2.2.2]octane and 1.4 g of the compound obtained in step C of EXAMPLE 4 in 5 ml of DMF is heated at 60° C. for 5 hours. After cooling to RT, the reaction mixture is poured into water and extracted with DCM, the organic phase is washed twice with 2 N HCl solution and three times with saturated Nacl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using DCM and then a DCM/MeOH mixture (92/8; v/v) as the eluent. The product obtained is taken up with ether and the precipitate formed i8 wrung to give 0.21 g of the expected product. M.p.=138° C.

後処理

  1. temperatureAfter cooling to RT
  2. extractionextracted with DCM
  3. washthe organic phase is washed twice with 2 N HCl solution and three times with saturated Nacl solution
  4. dry with materialdried over MgSO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica
  7. customThe product obtained
  8. customthe precipitate formed i8

出典と根拠

ORDレコード
ord-490d2f9fdee942e284353580d22fce6b
出典データセット
uspto-grants-2000_01
特許番号
US06011154

反応ノート

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