4-Aminocyclohexanol → HCID 28548490, compound
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[NH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1.C(O[Na])(C)(C)C.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:9][CH:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)=[N:3][CH:4]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 85 °C
Procedure
A mixture of 2-Chloro-5-methyl-pyridine (0.1 g, 0.78 mmol), 4-amino-cyclohexanol (0.117 g, 0.78 mmol), Pd2(dba)3 (0.057 g, 0.0624 mmol), t-BuONa (0.262 g, 2.73 mmol) and Binap (0.076 g, 0.1248 mmol) in toluene (10 mL) was stirred at 85° C. until TLC analysis confirmed the absence of starting materials. Then the mixture was diluted with water (10 mL), and extracted with EtOAc (3×20 mL). The combined organic extracts were washed with water (5 mL) and brine (10 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by column chromatography (EtOAc:Petrol ether=1:2) to provide 4-(5-methyl-pyridin-2-ylamino)-cyclohexanol (0.06 g, yield 60%) as a solid.
Workup
- extractionextracted with EtOAc (3×20 mL)
- washThe combined organic extracts were washed with water (5 mL) and brine (10 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- customThe filtrate was evaporated in vacuo
- customthe residue was purified by column chromatography (EtOAc:Petrol ether=1:2)
Sources & evidence
- ORD record
- ord-9bea4ea9a19d498b867563ff5dd56892
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952037B2
Reaction notes
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