1,2-Dichloroethane → (+/-)-6-[2-Methyl-4-(4-phenyl-azepan-1ylmethyl)-phenoxy]-nicotinonitrile

HRID 228245Notes

Reaction equation

HRID 228245 reaction equation
C1([CH:7]2[CH2:13][CH2:12][CH2:11][CH2:10][NH:9][CH2:8]2)C=CC=CC=1.[CH:14]([C:16]1[CH:30]=[CH:29][C:19]([O:20][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=2)=[C:18]([CH3:31])[CH:17]=1)=O.C(O[BH-](O[C:42](=O)[CH3:43])OC(=O)C)(=O)C.[Na+].[C:46](O)(=O)[CH3:47].Cl[CH2:51][CH2:52]Cl>C(OCC)(=O)C>[CH3:31][C:18]1[CH:17]=[C:16]([CH2:14][N:9]2[CH2:10][CH2:11][CH2:12][CH:13]([C:42]3[CH:43]=[CH:47][CH:46]=[CH:52][CH:51]=3)[CH2:7][CH2:8]2)[CH:30]=[CH:29][C:19]=1[O:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 236263713-PhenylazepaneHCID 597302456-(4-Formyl-2-methylphenoxy)nicotinonitrile2×

Product 1

HCID 59730055(+/-)-6-[2-Methyl-4-(4-phenyl-azepan-1ylmethyl)-phenoxy]-nicotinonitrileYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using a method similar to Example 365 step 2, using 3-phenyl-azapane (0.0957 g, 0.548 mmol), 6-(4-formyl-2-methyl-phenoxy)-nicotinonitrile (compound of example 365 step 1) (0.103 g, 0.420 mmol), sodium triacetoxyborohydride (0.110 g, 0.651 mmol), and acetic acid (0.03 mL, 0.594 mmol) in 1,2-dichloroethane (5.0 mL), provides, after silica gel chromatography (4:1→1:1 hexanes:ethyl acetate), 0.144 g (84%) of the title compound as a yellow oil: mass spectrum (electrospray): m/z=398.2 (M+1); 1H NMR (CDCl3): 8.47 (d, 1H, J=1.5 Hz), 7.91 (dd, 1H, J=1.5, 7.8 Hz), 7.33-7.25 (m, 4H), 7.25-7.21 (m, 2H), 7.21-7.15 (m, 1H), 7.03-6.97 (m, 2H), 3.73-3.67 (m, 2H), 2.90-2.81 (m, 2H), 2.79-2.66 (m, 3H), 2.15 (s, 3H), 2.01-1.67 (m, 6H).

Workup

  1. customprovides

Sources & evidence

ORD record
ord-fc8dd69725674ad08e2878cb261c3c72
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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