Hydrochloric Acid → 1-Benzoyl-3-[3-[4-benzyl-4-(pyrrolidin-1-ylcarbonyl)piperid-1-yl]propyl]-3-(3,4-dichlorophenyl)piperidine hydrochloride hemihydrate

HRID 50067노트

반응식

HRID 50067 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=[O:8])=[CH:3][CH:2]=1.[CH2:12]([C:19]1([C:25]([N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:26])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[ClH:32].[C:33]([N:41]1[CH2:46][CH2:45][CH2:44][C:43]([C:63]2[CH:68]=[CH:67][C:66]([Cl:69])=[C:65]([Cl:70])[CH:64]=2)([CH2:47][CH2:48][CH2:49][N:50]2[CH2:55][CH2:54][CH:53]([C:56]([N:58]3[CH2:62][CH2:61][CH2:60][CH2:59]3)=[O:57])[CH2:52][CH2:51]2)[CH2:42]1)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.O>[OH2:8].[ClH:69].[C:33]([N:41]1[CH2:46][CH2:45][CH2:44][C:43]([CH2:47][CH2:48][CH2:49][N:22]2[CH2:23][CH2:24][C:19]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:25]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:26])[CH2:20][CH2:21]2)([C:63]2[CH:68]=[CH:67][C:66]([Cl:69])=[C:65]([Cl:70])[CH:64]=2)[CH2:42]1)(=[O:40])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1.[C:33]([N:41]1[CH2:46][CH2:45][CH2:44][C:43]([C:63]2[CH:68]=[CH:67][C:66]([Cl:69])=[C:65]([Cl:70])[CH:64]=2)([CH2:47][CH2:48][CH2:49][N:50]2[CH2:51][CH2:52][C:53]([C:56]([N:58]3[CH2:59][CH2:60][CH2:61][CH2:62]3)=[O:57])([CH2:11][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:54][CH2:55]2)[CH2:42]1)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[ClH:32]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 227417124-Benzyl-4-(pyrrolidin-1-ylcarbonyl)piperidine p-toluenesulfonateHCID 227417141-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-[4-(pyrrolidin-1-ylcarbonyl)piperid-1-yl]propyl]piperidine hydrochloride

생성물 1

HCID 1317216551-Benzoyl-3-[3-[4-benzyl-4-(pyrrolidin-1-ylcarbonyl)piperid-1-yl]propyl]-3-(3,4-dichlorophenyl)piperidine hydrochloride hemihydrate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A mixture of 4-benzyl-4-(pyrrolidin-1-ylcarbonyl)piperidine p-toluene-sulfonate, 0.65 g of the compound obtained in step B of EXAMPLE 1 and 0.7 g of K2CO3 in 6 ml of DMF is heated at 80° C. for 3 hours. The reaction mixture is poured into iced water and the precipitate formed is filtered off and washed with water. The precipitate is dissolved in AcOEt, the organic phase is dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica H using DCM and then a DCM/MeOH mixture (95/5; v/v) as the eluent. The product obtained is taken up with ethereal hydrogen chloride and the precipitate formed is filtered off to give 0.56 g of the expected product.

후처리

  1. customthe precipitate formed
  2. filtrationis filtered off
  3. washwashed with water
  4. dissolutionThe precipitate is dissolved in AcOEt
  5. dry with materialthe organic phase is dried over MgSO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica H
  8. customThe product obtained
  9. customthe precipitate formed
  10. filtrationis filtered off

출처 및 근거

ORD 기록
ord-960e5a400a17473e86c5082ea882ad5d
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710042B2

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