Butanal → Benzenemethanamine, N-butyl-4-chloro-

HRID 528895Notes

Reaction equation

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

Participants

Reactant 2

HCID 261Butanal

HCID 660364-Chlorobenzylamine

Product 1

HCID 485399Benzenemethanamine, N-butyl-4-chloro-Yield 40.2%

Procedure

Following a procedure analogous to that for the synthesis of Example 106, (4-chlorophenyl)methanamine (750 mg, 5.30 mmol) and butyraldehyde (480 μL, 5.30 mmol) were converted to the title compound (421 mg, 40%). 1H NMR (CDCl3) δ 7.55 (d, J=8.4 Hz, 2H), 7.41-7.34 (m, 2H), 3.98 (s, 2H), 2.78-2.70 (m, 2H), 1.79 (td, J=7.7, 15.6 Hz, 2H), 1.36 (qd, J=7.4, 15.1 Hz, 2H), 0.95-0.88 (m, 4H); MS(ESI+) m/z 198.1 (M+H)+.

Sources & evidence

ORD record: ord-580b6b7e514946fd8e5a2eac89839b29
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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