Hydrochloric Acid → 4-[4-(1-Pyrrolidinyl)-1-piperidinyl]benzonitrile

HRID 1199797Notes

Reaction equation

HRID 1199797 reaction equation
[N:1]1([C:6]2[CH2:7][CH2:8][N:9]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[CH2:10][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(Cl)Cl.C([BH3-])#N.C([N+](CCCC)(CCCC)CCCC)CCC>C([O-])([O-])=O.[Na+].[Na+]>[N:1]1([CH:6]2[CH2:7][CH2:8][N:9]([C:12]3[CH:13]=[CH:14][C:15]([C:16]#[N:17])=[CH:18][CH:19]=3)[CH2:10][CH2:11]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 2724287Tetrabutylammonium (cyano-C)trihydroborateHCID 146267924-(3,6-Dihydro-4-(1-pyrrolidinyl)-1(2H)-pyridinyl]benzonitrile

Product 1

HCID 113343154-[4-(1-Pyrrolidinyl)-1-piperidinyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

A solution of 2 g (0.0079 mol) of the compound of (C), 5 ml of 4.66M HCl (in isopropyl alcohol), 40 ml of methylene chloride and 4.46 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 the title compound. An analytical sample is prepared by recrystallization from cyclohexane: m.p. 88°-89° C.; IR (KBr) 2200, 1600, and 820 cm-1 ; NMR (CDCl3) δ7.45 (d, 2H), 6.85 (d, 2H), 4.0-3.7 (m, 1H), 2.95-2.65 (m, 8H), and 2.15-1.65 (m, 8H); M.S. m/e 256 (M+1).

Workup

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

Sources & evidence

ORD record
ord-542cd8166ec243269e75afe727080f9f
Source dataset
uspto-grants-1990_02
Patent number
US04902800

Reaction notes

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