Butylamine → Benzenemethanamine, N-butyl-3,4-dichloro-

HRID 528887Notes

Reaction equation

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

Participants

Reactant 2

HCID 8007Butylamine

HCID 227103,4-Dichlorobenzaldehyde

Product 1

HCID 485439Benzenemethanamine, N-butyl-3,4-dichloro-Yield 53.5%

Procedure

Following a procedure analogous to that for the synthesis of Example 106, 3,4-dichlorobenzaldehyde (10.0 g, 57.1 mmol) and butan-1-amine (4.18 g, 57.1 mmol) were converted to the title compound (7.09 g, 53%). 1H NMR (CDCl3) δ 7.45 (d, J=2.0 Hz, 1H), 7.40 (d, J=8.1 Hz, 1H), 7.19 (dd, J=2.0, 8.1 Hz, 1H), 3.79 (s, 2H), 2.68-2.59 (m, 2H), 1.59-1.45 (m, 2H), 1.36 (qd, J=7.3, 15.0 Hz, 2H), 0.92 (t, J=7.4 Hz, 3H); MS (ESI+) m/z 232.1 (M+H)+.

Sources & evidence

ORD record: ord-a925544797b54c3aad9e1361acc889c0
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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