1,4-Dioxane → 1-Butanol, 4,4'-iminobis-

HRID 1488309Notes

Reaction equation

HRID 1488309 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18]CC1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>O>[NH:13]([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[CH2:12][CH2:11][CH2:10][CH2:9][OH:8]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 117996041HCID 117996041, compound

Product 1

HCID 1575181-Butanol, 4,4'-iminobis-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of bis(4-(benzyloxy)butyl)amine (300 mg, 0.879 mmol) was in a mixed solvent of Dioxane (5 ml)/Water (5 mL), was added PdOH2 (30.8 mg, 0.044 mmol). The reaction was stirred under H2 at 40 PSI for 18 h. LC-MS showed no starting material and formation of desired product. The mixture was filtered through a pad of celite, washed with dioxane/water (10 mL, 1/1). The filtrate was concentrated and dried over high vacuum pump to give the titled compound (130 mg, 0.806 mmol, 92% yield). LC-MS Method A: m/e=162.01 [M+1]; Rt=0.18 min.

Sources & evidence

ORD record
ord-791cf1034a444684b1b2318fa3ed7283
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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