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

HRID 1376065Notes

Reaction equation

HRID 1376065 reaction equation
[CH:1]1([CH2:7][CH:8]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Si]([C:14]#[N:15])(C)(C)C.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>CO>[C:19]([O:18][C:16]([N:23]1[CH2:28][CH2:27][N:26]([CH:8]([C:14]#[N:15])[CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:25][CH2:24]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 3166272-Cyclohexylacetaldehyde

Product 1

HCID 587863884-(1-Cyano-2-cyclohexyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of cyclohexaneacetaldehyde (8.45 g, 66.96 mmol) and TMSCN (17.9 mL, 133.92 mmol) in MeOH was stirred for 2 h at 23° C. and N-BOC-piperazine (13.72 g, 73.66 mmol) was added. After 24 the solvent was evaporated to give the title compound.

Workup

  1. customAfter 24 the solvent was evaporated

Sources & evidence

ORD record
ord-37bb2fcfb2e74a95b88a83695df3355e
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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