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Hydrochloric Acid → 1-[4-(Methylsulfonyl)phenyl]-4-(1-pyrrolidinyl)piperidine

HRID 1199799
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HRID 1199799 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH:15]=[C:14]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.C(Cl)Cl.C([BH3-])#N.C([N+](CCCC)(CCCC)CCCC)CCC>C([O-])([O-])=O.[Na+].[Na+]>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:12][CH2:13][CH:14]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:15][CH2:16]2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 2724287Tetrabutylammonium (cyano-C)trihydroborateHCID 146267951,2,3,6-Tetrahydro-1-[4-(methylsulfonyl)phenyl]-4-(1-pyrrolidinyl)pyridine

생성물 1

HCID 146992121-[4-(Methylsulfonyl)phenyl]-4-(1-pyrrolidinyl)piperidine수율 80%

시약·촉매·용매 1

HCID 10340
Sodium Carbonate
용매

실험 절차

A solution of 2 g (0.0065 mol) of the compound of (C), 5 ml of 4.66M HCl (in isopropyl alcohol), 40 ml of methylene chloride and 2.68 g of tetrabutylammonium cyanoborohydride is stirred at ambient temperature overnight. The solution is diluted with sat. Na2CO3 solution and extracted with methylene chloride. The combined extracts are dried (Na2SO4) and concentrated in vacuo to give 1.6 g (80%) of the title compound. An analytical sample is prepared by recrystallization from ethyl acetate: m.p. 166°-170° C.; IR (KBr) 1595, 1295, and 880 cm-1 ; NMR (CDCl3)δ7.75 (d, 2H); 6.9 (d, 2H), 4.0-3.7 (m, 1H), 3.15-2.55 (m, 8H), 3.0 (s, 3H), and 2.05-1.55 (m, 8H)

후처리

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined extracts are dried (Na2SO4)
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3fa4e989ec6c458aba45954599a9be76
출처 데이터셋
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04902800

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