Triethanolamine → HCID 86700943, compound

HRID 1522912Notes

Reaction equation

[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[C:13]([O:17][C:18](=[O:21])[CH2:19]Br)([CH3:16])([CH3:15])[CH3:14].N(CCO)(CCO)CCO.[NH4+].[Cl-]>O1CCCC1.O.CN(C=O)C>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:19][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:21])[CH2:9][CH2:8]1

Participants

Conditions

Temperature: 50 °C

Procedure

1-[2-(2-hydroxyethoxyl)ethyl]piperizine (12.36 g, 71.8 mmol) in tetrahydrofuran (THF) (60 mL) was added to bromoacetic acid tert-butyl ester (14.00 g, 71.8 mmol) in THF (10 mL). Triethanolamine (TEA) (22 mL, 143.5 mmol) was then added. DMF (30 mL) was added to the mixture to dissolve any solids. The reaction mixture was stirred at 50° C. for approximately 16 hours (overnight). NH4Cl (20 g, 370 mmol) and water (20 mL) were added to the mixture. The organic layer was extracted with ethylacetate (EtOAc). The organic layers were combined, concentrated, and purified by silica gel column chromatography (5-10% methanol (MeOH) in ethylacetate) to give of the target product as an oil (16 g, 77% yield). 1H NMR (400 MHz, CDCl3) (ppm) 3.70-3.55 (m, 7H), 3.09 (s, 2H), 2.52-2.80 (m, 10H), 1.44 (s, 9H).

Workup

dissolutionto dissolve any solids
extractionThe organic layer was extracted with ethylacetate (EtOAc)
concentrationconcentrated
custompurified by silica gel column chromatography (5-10% methanol (MeOH) in ethylacetate)

Sources & evidence

ORD record: ord-80dd0352aeb34d1a83b84b18d3551330
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09078926B2

Reaction notes

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