Hexylamine → [2-(Hexylamino)phenyl]methanol

HRID 2179282

Reaction equation

Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[CH2:10]([NH2:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>>[CH2:10]([NH:16][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

Reactant 2

HCID 8102Hexylamine

HCID 728502-Bromobenzyl alcohol

Product 1

HCID 15084054[2-(Hexylamino)phenyl]methanolYield 81%

Procedure

Using the general procedure, 2-bromobenzyl alcohol (187 mg, 1.0 mmol) was coupled with n-hexylamine (198 μL, 1.5 mmol) at 90° C. for 22 h. Purification of the crude product by column chromatography on silica gel using hexane/ethyl acetate (6:1) as eluent afforded the desired product as a colorless liquid (168 mg, 81% yield). Rf=0.7 (hexane/ethyl acetate=2:1).

Workup

customPurification of the crude product by column chromatography on silica gel

Sources & evidence

ORD record: ord-f5dc8fc5fa824427be8b4e7c7fb7c6b0
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067955B2

Linked notes

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