Water → 3-[4-(Benzyloxy)-3-methoxyphenyl]propan-1-amine

HRID 458789Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([NH2:19])=O)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[H-]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][NH2:19])=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-(4-benzyloxy-3-methoxy-phenyl)-propionamide (7.85 g, 27.53 mmol) in anhydrous THF (210 ml) was slowly added to a stirred, ice-cooled suspension of LiAlH4 (2.09 g, 55.07 mmol) in anhydrous THF (90 ml). Upon completion of the addition, the mixture was stirred at reflux for 1 h. After cooling to 0° C., H2O (15 ml) was added dropwise to decompose the excess of hydride, and the resulting suspension was then filtered. The residue after evaporation was partitioned between H2O (50 ml) and CH2Cl2 (100 ml). The organic layer was washed with NaHCO3 and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure to give the crude. amine (6.03 g, 22.22 mmol, 81%) as a yellow oil.

Workup

temperaturecooled
additionUpon completion of the addition
temperatureat reflux for 1 h
filtrationthe resulting suspension was then filtered
customThe residue after evaporation
customwas partitioned between H2O (50 ml) and CH2Cl2 (100 ml)
washThe organic layer was washed with NaHCO3 and brine
dry with materialdried over anhydrous MgSO4
concentrationconcentrated under reduced pressure
customto give the crude

Sources & evidence

ORD record: ord-f8b3238fdd0f46e78a28c83242ac99f8
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192950B2

Reaction notes

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