Butanal → HCID 63046144, compound

HRID 528888Notes

Reaction equation

HRID 528888 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][NH2:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:12](=O)[CH2:13][CH2:14][CH3:15]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[CH2:9][CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

3

Reactant 2

HCID 261ButanalHCID 2179583,4-Dichlorophenethylamine

Product 1

HCID 63046144HCID 63046144, compoundYield 24%

Procedure

Following a procedure analogous to that for the synthesis of Example 106, 2-(3,4-dichlorophenyl)ethanamine (1.27 g, 6.68 mmol) and butyraldehyde (600 μL, 6.68 mmol) were converted to the title compound (390 mg, 24%). 1H NMR (CDCl3) δ 7.37 (d, J=8.1 Hz, 1H), 7.32 (d, J=2.0 Hz, 1H), 7.06 (dd, J=2.1, 8.3 Hz, 1H), 2.97-2.90 (m, 2H), 2.88-2.81 (m, 2H), 2.75-2.66 (m, 2H), 1.53 (quin, J=7.5 Hz, 2H), 1.34 (qd, J=7.4, 15.0 Hz, 2H), 0.92 (t, J=7.3 Hz, 3H); MS(ESI+) m/z 246.1 (M+H)+.

Sources & evidence

ORD record
ord-9f53a8778e2040e69a6030177a14557a
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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