Dimethylamine, hydrochloride → 2,6-Diisopropyl-3-(dimethylamino)methyl-4-(4-fluorophenyl)-5-pentyl-pyridine

HRID 324835Notes

Reaction equation

HRID 324835 reaction equation
[CH:1]([C:4]1[C:9]([CH:10]=O)=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:7]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:6]([CH:24]([CH3:26])[CH3:25])[N:5]=1)([CH3:3])[CH3:2].Cl.[CH3:28][NH:29][CH3:30]>CCOCC.C(Cl)Cl>[CH:1]([C:4]1[C:9]([CH2:10][N:29]([CH3:30])[CH3:28])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:7]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:6]([CH:24]([CH3:26])[CH3:25])[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10473Dimethylamine, hydrochlorideHCID 220049662,6-Diisopropyl-4-(4-fluorophenyl)-5-pentyl-3-pyridine-carboxaldehyde

Product 1

HCID 220050452,6-Diisopropyl-3-(dimethylamino)methyl-4-(4-fluorophenyl)-5-pentyl-pyridine

Reagents, catalysts & solvents 1

HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

The title compound was prepared from 2,6-diisopropyl-4-(4-fluorophenyl)-5-pentyl-3-pyridinecarboxaldehyde (Example 114, Step A) and dimethylamine hydrochloride, according to the procedures described in Example 120. 1H NMR (300 MHz, CDCl3): δ 7.09 (m, 4 H), 3.49 (septet, J=6.6 Hz, 1 H), 3.21 (septet, J=6.6 Hz, 1 H), 3.05 (s, 2 H), 2.22 (t, J=5.2 Hz, 2 H), 1.99 (s, 6 H), 1.18 (m, 18 H), 0.790 (t, J =6.3 Hz, 3 H). FAB-MS: calcd for (C25H37FN2) 384, found 385 (M+H). Anal. Calcd for C23H37FN2: C, 78.08; H, 9.70; N, 7.28; F, 4.94. Found: C, 77.95; H, 9.66; N, 7.12; F, 5.25. mp 69-71° C. Rf=0.4 (20% ether/CH2Cl2).

Sources & evidence

ORD record
ord-5a2e642776cc415db73cfa743f18eb10
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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