Sodium Hydroxide → HCID 178507633, compound

HRID 240743Notes

Reaction equation

Cl[O-].[Na+].[OH-].[NH4+:5].[Cl-].[NH4+].[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1.[OH-].[Na+]>C1COCC1.O>[NH:5]=[C:9]1[CH2:10][CH:11]([CH2:14][CH2:15][OH:16])[CH2:12][CH2:13][NH:8]1

Participants

Conditions

Temperature: -10 °C

Procedure

A 50 mL four-necked flask was charged with sodium hypochlorite solution (8.44 g, 7.00 mL, 15.5 mmol, Eq: 4) and the solution was cooled to −10° C. Maintaining this temperature, ammonium hydroxide 25% NH3 (949 mg, 1.05 ml, 13.9 mmol, Eq: 3.6) and ammonium chloride 1M (11.6 mL, 11.6 mmol, Eq: 3) were added simultaneously. After 5 min, 2-(piperidin-4-yl)ethanol (500 mg, 3.87 mmol, Eq: 1.00, CAN 622-26-4) in 2 mL THF and sodium hydroxide (2.58 g, 1.94 mL, 19.3 mmol, Eq: 5) were added simultaneously at the same temperature as before, and the reaction allowed to proceed for another 2 hours at rt. The mixture was diluted with H2O and extracted with EtOAc (2×10 mL). The aqueous layer was concentrated in vacuo and the residue taken up in CH2Cl2, dried over Na2SO4, filtered and concentrated in vacuo. Thereby, 340 mg of 2-(1-mino-piperidin-4-yl)-ethanol were obtained as white semi-solid; MS (EI) 145.2 (M+H)+.

Workup

additionwere added simultaneously
waitto proceed for another 2 hours at rt
extractionextracted with EtOAc (2×10 mL)
concentrationThe aqueous layer was concentrated in vacuo
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-61af258f223645e7a6abebc0aa2c4913
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648099B2

Reaction notes

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