Butanal → N-(3-Isopropoxybenzyl)butan-1-amine

HRID 528891Notes

Reaction equation

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

Participants

Reactant 2

HCID 261Butanal

HCID 27609351-(3-Isopropoxyphenyl)methanamine

Product 1

HCID 39245116N-(3-Isopropoxybenzyl)butan-1-amineYield 16.1%

Procedure

Following a procedure analogous to that for the synthesis of Example 106, (3-isopropoxyphenyl)methanamine (Matrix, 200 mg, 1.21 mmol) and butyraldehyde (110 μL, 1.21 mmol) were converted to the title compound (43 mg, 16%). 1H NMR (CDCl3) δ 7.29-7.17 (m, 1H), 6.99-6.74 (m, 3H), 4.57 (td, J=6.1, 12.1 Hz, 1H), 3.80 (s, 2H), 2.65 (t, J=7.3 Hz, 2H), 1.63-1.50 (m, 2H), 1.40-1.24 (m, 8H), 0.90 (t, J=7.3 Hz, 3H); MS (ESI+) m/z 222.2 (M+H)+.

Sources & evidence

ORD record: ord-3f508e031e714908a062273ee0ee9b69
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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