Cyclohexanone → HCID 9835935, compound

HRID 1790012Notes

Reaction equation

HRID 1790012 reaction equation
[N:1]1([C:6]2[CH:18]=[CH:17][C:9]([O:10][CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:19]1(=O)[CH2:24][CH2:23]CCC1.[CH2:26]([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH:11]3[CH2:12][CH2:13][N:14]([CH2:26][CH:24]([CH3:23])[CH3:19])[CH2:15][CH2:16]3)=[CH:17][CH:18]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 7967CyclohexanoneHCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 220369104-[4-(1H-Imidazol-1-yl)phenoxy]piperidine

Product 1

HCID 9835935HCID 9835935, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 6 (130 mg), cyclohexanone (0.06 mL), and dibutyltin dichloride (3 mg) in THF (0.1 mL) was treated with phenylsilane (0.07 mL). After 16 h, the resulting mixture was chromatographed (0-8% 2M methanolic ammonia/DCM), giving the title compound as a waxy solid (18 mg). 1H NMR (400 MHz, CDCl3): 7.75 (t, J=1.2 Hz, 1H), 7.28 (d, J=9.0 Hz, 2H), 7.20 (t, J=1.4 Hz, 1H), 7.18 (t, J=1.2 Hz, 1H), 6.99 (d, J=8.8 Hz, 2H), 4.35-4.27 (m, 1H), 2.76-2.67 (m, 2H), 2.26-2.18 (m, 2H), 2.10 (d, J=7.24 Hz, 2H), 2.05-1.96 (m, 2H), 1.87-1.73 (m, 3H), 0.90 (d, J=6.5 Hz, 6H).

Workup

  1. customthe resulting mixture was chromatographed (0-8% 2M methanolic ammonia/DCM)

Sources & evidence

ORD record
ord-e3fc973aa2db4d2bb873ff11623b4a2f
Source dataset
uspto-grants-2006_07
Patent number
US07071191B2

Reaction notes

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