Trimethylsilyl cyanide → HCID 68866956, compound

HRID 1817225Notes

Reaction equation

HRID 1817225 reaction equation
[N:1]12[CH2:8][CH2:7][C:4]([C:9]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)O)([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[Al+3].[Cl-].[Cl-].[Cl-].[Si]([C:29]#[N:30])(C)(C)C>ClCCCl>[N:1]12[CH2:8][CH2:7][C:4]([C:9]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)[C:29]#[N:30])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) ChlorideHCID 688655991-Azabicyclo[2.2.2]oct-4-yl(di-2-thienyl)methanol

Product 1

HCID 68866956HCID 68866956, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Following the general procedure for cyano formation outlined in Example 1, 1-azabicyclo[2.2.2]oct-4-yl(di-2-thienyl)methanol (0.3065 g, 1.003 mmol), AlCl3 (0.661 g, 4.99 mmol) and TMSCN (0.66 mL, 4.95 mmol) in 1,2-dichloroethane (17.0 mL) were reacted to give the desired product (0.1073 g, 34.1%). EI-MS m/z 315 (M+) Rt (1.65 min).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-d0d9d46f02de432dab68e1c2a4c4fe04
Source dataset
uspto-grants-2009_10
Patent number
US07598267B2

Reaction notes

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