Cyclohexylamine → HCID 71580561, compound

HRID 2273851Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>>[Si:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:22][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

Reactant 3

HCID 7965Cyclohexylamine

HCID 11430Potassium Carbonate

HCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilane

Product 1

HCID 71580561HCID 71580561, compoundYield 90.6%

Conditions

Temperature: 80 °C

Procedure

In a sealed tube was charged with ((6-bromohexyl)oxy)(tert-butyl)dimethylsilane (2.35 mL, 8.45 mmol), cyclohexanamine (1.95 mL, 16.9 mmol), potassium carbonate (2.34 g, 16.9 mmol), and acetonirile (6 mL). The mixture was stirred at 80° C. for 2.5 days and filtered through a pad of celite. The solution was concentrated and purified on silica gel with a eluent of Methanol (2N NH3):methylene chloride from 0:1 to 5:95 to give a clear oil (2.4 g, 90%). 1H NMR (300 MHz, CDCl3): δ 3.55 (t, J=6.4 Hz, 2H), 2.56 (t, J=7.0 Hz, 2H), 2.42-2.28 (m, 1H), 1.89-1.78 (m, 2H), 1.74-1.62 (m, 2H), 1.62-1.52 (m, 2H), 1.52-1.36 (m, 4H), 1.36-1.22 (m, 5H), 1.22-0.92 (m, 5H), 0.85 (s, 9H), 0.05 (s, 6H).

Workup

filtrationfiltered through a pad of celite
concentrationThe solution was concentrated
custompurified on silica gel with a eluent of Methanol (2N NH3)

Sources & evidence

ORD record: ord-e044dd146cc849ff834793bfb8d83697
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126937B2

Reaction notes

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