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

HRID 1199799Notes

Reaction equation

HRID 1199799 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

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)

Workup

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

Sources & evidence

ORD record
ord-3fa4e989ec6c458aba45954599a9be76
Source dataset
uspto-grants-1990_02
Patent number
US04902800

Reaction notes

Loading…