Carbon Tetrachloride → Tert-butyl 4-(4-cyanophenyl)piperidine-1-carboxylate

HRID 1756999Notes

Reaction equation

HRID 1756999 reaction equation
[NH2:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:19]([O:18][C:16]([N:13]1[CH2:12][CH2:11][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([C:2]#[N:1])=[CH:9][CH:8]=2)[CH2:15][CH2:14]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 5943Carbon Tetrachloride2×HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 224929041,1-Dimethylethyl 4-[4-(aminocarbonyl)phenyl]-1-piperidinecarboxylate

Product 1

HCID 22492960Tert-butyl 4-(4-cyanophenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 4.5 g of 4-(4-aminocarbonylphenyl)-1-tert.butyloxycarbonyl-piperidine, 6.8 g of triphenylphosphine, 2.4 g of carbon tetrachloride and 1.6 g of triethylamine in 50 ml of chloroform is stirred for 2 hours at 60° C. 1 ml of carbon tetrachloride is added dropwise and the mixture is stirred for a further 3 hours at 60° C. The solvent is removed under reduced pressure and the remaining oil is chromatographed over silica gel. Yield: 2.4 g (57% of theory), Rf value: 0.32 (silica gel; cyclohexane/ethyl acetate=4:1)

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe remaining oil is chromatographed over silica gel

Sources & evidence

ORD record
ord-017d65bd05704ed39b4d8559ba1c6f3c
Source dataset
uspto-grants-1995_08
Patent number
US05442064

Reaction notes

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