Water → C-[1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidin-3-yl]methylamine

HRID 2407299Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH2:9][CH:8]1[CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH:20]([C:24]([NH2:26])=O)[CH2:19]1.O>C1COCC1>[O:7]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH2:9][CH:8]1[CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH:20]([CH2:24][NH2:26])[CH2:19]1

Participants

Conditions

Temperature: 66 °C

Procedure

To a suspension of LiAlH4 (0.62 g, 16.30 mmol) in dry THF (15 ml) was added 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-piperidine-3-carboxylic acid amide (0.45 g, 01.63 mmol) in dry THF (5 ml). The reaction mixture was heated under microwaves at 66° C. for 1 h. Water was slowly added and the mixture extracted with EtOAc (3×20 ml). The combined organic phases were dried (Na2SO4), filtered and the filtrate was evaporated to give the desired product, which was purified by column chromatography (DCM/MeOH, 98:2).

Workup

extractionthe mixture extracted with EtOAc (3×20 ml)
dry with materialThe combined organic phases were dried (Na2SO4)
filtrationfiltered
customthe filtrate was evaporated

Sources & evidence

ORD record: ord-cba4079d066b47a786480f364fb5f9cc
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809536B2

Reaction notes

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