Ethanolamine → 2-((3-Cyclohexylpropyl)amino)ethanol

HRID 1183125Notes

Reaction equation

HRID 1183125 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[CH:5]1([CH2:11][CH2:12][CH:13]=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:5]1([CH2:11][CH2:12][CH2:13][NH:4][CH2:3][CH2:1][OH:2])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 78070CyclohexanepropionaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 5417632-((3-Cyclohexylpropyl)amino)ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethanolamine (0.44 g, 7.1 mmol) in DCM (15 mL) at 0° C. was added a solution of 3-cyclohexylpropionaldehyde (1.0 g, 7.1 mmol) in DCM (10 mL) followed by sodium triacetoxyborohydride (1.67 g, 7.86 mmol). The resulting mixture was warmed to room temperature. After 2.5 hours the desired product was observed by mass spectrometric analysis. The reaction mixture was stirred overnight, then diluted with DCM (50 mL), washed with saturated sodium bicarbonate (2×50 mL), and brine (50 mL), dried over sodium sulfate, filtered, and concentrated to give a clear oil (1.0 g) which was used in the next step without further purification. ((m/z): [M+H]+ calcd for C11H23NO, 186.20; found, 186.0).

Sources & evidence

ORD record
ord-5aec0a687bb344d796213c915f41b08f
Source dataset
uspto-grants-2014_03
Patent number
US08664242B2

Reaction notes

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