Butanal → Benzenemethanamine, N-butyl-3-chloro-

HRID 528894Notes

Reaction equation

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

Participants

Reactant 2

HCID 261Butanal

HCID 77802Benzenemethanamine, 3-chloro-

Product 1

HCID 457585Benzenemethanamine, N-butyl-3-chloro-Yield 32%

Procedure

Following a procedure analogous to that for the synthesis of Example 106, (3-chlorophenyl)methanamine (750 mg, 5.30 mmol) and butyraldehyde (480 μL, 5.30 mmol) were converted to the title compound (331 mg, 32%). 1H NMR (CDCl3) δ 7.64-7.55 (m, 2H), 7.44-7.33 (m, 2H), 4.02 (s, 2H), 2.84-2.72 (m, 2H), 1.84 (td, J=7.8, 15.8 Hz, 2H), 1.38 (sxt, J=7.5 Hz, 2H), 0.91 (t, J=7.4 Hz, 3H); MS(ESI+) m/z 198.1 (M+H)+.

Sources & evidence

ORD record: ord-b0eeef2b06914b77853cf642e0119a8e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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