Hydrochloric Acid → 3-[3-[4-(Acryloyl-N-methylamino)-4-phenylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)piperidine hydrochloride

HRID 50060ノート

反応式

HRID 50060 の反応式
Cl.[C:2]([N:6]([C:8]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[CH3:7])(=[O:5])[CH:3]=[CH2:4].Cl.[C:21]([N:29]1[CH2:34][CH2:33][CH2:32][C:31]([C:51]2[CH:56]=[CH:55][C:54]([Cl:57])=[C:53]([Cl:58])[CH:52]=2)([CH2:35][CH2:36][CH2:37]N2CCC(C(N3CCCC3)=O)CC2)[CH2:30]1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.C(Cl)Cl.O>[ClH:57].[C:2]([N:6]([C:8]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:10][N:11]([CH2:37][CH2:36][CH2:35][C:31]2([C:51]3[CH:56]=[CH:55][C:54]([Cl:57])=[C:53]([Cl:58])[CH:52]=3)[CH2:32][CH2:33][CH2:34][N:29]([C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:30]2)[CH2:12][CH2:13]1)[CH3:7])(=[O:5])[CH:3]=[CH2:4]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 227417141-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-[4-(pyrrolidin-1-ylcarbonyl)piperid-1-yl]propyl]piperidine hydrochlorideHCID 227417164-(acryloyl-N-methylamino)-4-phenylpiperidine hydrochloride

生成物 1

HCID 227417863-[3-[4-(Acryloyl-N-methylamino)-4-phenylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)piperidine hydrochloride収率 80.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

A mixture of 0.27 g of 4-(acryloyl-N-methylamino)-4-phenylpiperidine hydrochloride, 0.45 g of the compound obtained in step B of EXAMPLE 1 and 0.3 g of K2CO3 in 3 ml of DMF is heated at 80° C. for 2 hours. The reaction mixture is poured into water and extracted with AcOEt, the organic phase is washed with water and with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a gradient of a DCM/MeOH mixture (99/1; v/v to 95/5; v/v) as the eluent. The product obtained is dissolved in DCM and acidified by the addition of ethereal hydrogen chloride and the precipitate formed is filtered off to give 0.2 g of the expected product, m.p.=128° C.

後処理

  1. extractionextracted with AcOEt
  2. washthe organic phase is washed with water and with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. customthe solvent is evaporated off under vacuum
  5. customThe residue is chromatographed on silica using a gradient of a DCM/MeOH mixture (99/1; v/v to 95/5; v/v) as the eluent
  6. customThe product obtained
  7. customthe precipitate formed
  8. filtrationis filtered off

出典と根拠

ORDレコード
ord-46ecda990008405c9949a5902ceea459
出典データセット
uspto-grants-2004_03
特許番号
US06710042B2

反応ノート

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