4-(1-Cyano-2-cyclohexyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester → 4-(2-Cyclohexyl-1-cyclohexylmethyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1376066Notes

Reaction equation

HRID 1376066 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:22]#N)[CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24]1(C[Mg]Br)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH:14]([CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:22][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 587863884-(1-Cyano-2-cyclohexyl-ethyl)-piperazine-1-carboxylic acid tert-butyl esterHCID 178419664HCID 178419664, compound

Product 1

HCID 587867634-(2-Cyclohexyl-1-cyclohexylmethyl-ethyl)-piperazine-1-carboxylic acid tert-butyl esterYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(1-cyano-2-cyclohexyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (1.81, 5.65 mmol) in THF (20 mL) and cyclohexylmethylmagnesium bromide (1.51 g, 22.60 mmol, 0.4 M in Et2O) was stirred at 23° C. for 24 h. The reaction was quenched with EtOAc and washed with brine, dried (Na2SO4), and evaporated. Final purification by flash chromatography (hexane-EtOAc 15:1) afforded 1020 mg of the title compound. MS m/z 393.3 (M++1).

Workup

  1. customThe reaction was quenched with EtOAc
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customFinal purification by flash chromatography (hexane-EtOAc 15:1)

Sources & evidence

ORD record
ord-c572a3382a7149eea6f9ca3a2e89b9cf
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

Loading…