N-Methyl-1-[3-(1-methylpiperidin-4-yl)phenyl]methanamine → HCID 178486906, compound

HRID 1295742Notes

Reaction equation

[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[CH:5]=1.Cl[C:18]1[NH:19][C:20]2[C:25]([C:26](=[O:28])[N:27]=1)=[C:24]([CH3:29])[C:23]([O:30][CH3:31])=[C:22]([O:32][CH3:33])[CH:21]=2>CCO>[CH3:31][O:30][C:23]1[C:24]([CH3:29])=[C:25]2[C:20](=[CH:21][C:22]=1[O:32][CH3:33])[NH:19][C:18]([N:2]([CH3:1])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)[CH:5]=1)=[N:27][C:26]2=[O:28]

Participants

Conditions

Temperature: 120 °C

Procedure

In a heavy-walled pressure tube, a mixture of methyl-[3-(1-methylpiperidin-4-yl)benzyl]amine (0.14 g, 0.64 mmol) and 2-chloro-6,7-dimethoxy-5-methyl-1H-quinazolin-4-one (0.155 g, 0.60 mmol) in 4 mL of EtOH, was heated to 120° C. for 5 hours. After solvent removal, the residue was purified by flash chromatography eluting with CH2Cl2:MeOH:NH4OH (94.5:5:0.5), and the above-titled Example H-3 crystallized from CH2Cl2/cyclohexane. mp 155.7–158° C.; IR (KBr) νmax 2933, 1651, 1590 cm−1; 1H NMR (DMSO-d6, 2.49) δ 1.59–1.71 (m, 4H), 1.93 (m, 2H), 2.16 (s, 3H), 2.42 (m, 1 H), 2.60 (s, 3H), 2.82 (m, 2 H), 3.01 (s, 3H), 3.62 (s, 3H), 3.84 (s, 3H), 4.78 (s, 2H), 6.63 (br s, 1H), 7.03 (d, 1H, J=7.44), 7.11–7.13 (m, 2 H), 7.25 (t, 1H, J=7.74), 10.81 (br s, D2O, 1H); 13C NMR (DMSO-d6, 39.50) δ 13.44, 32.94, 35.12, 41.08, 46.09, 51.64, 55.44, 55.65, 59.76, 124.61, 125.32, 125.65, 128.44, 137.54, 146.43; MS (ES+) m/z 437 (M+H); Anal. (C25H32N4O3.0.25H2O)C: calcd, 68.08; found, 68.02; H: calcd, 7.43; found, 7.19; N: calcd, 12.70; found, 12.69.

Workup

customAfter solvent removal
customthe residue was purified by flash chromatography
washeluting with CH2Cl2:MeOH:NH4OH (94.5:5:0.5)

Sources & evidence

ORD record: ord-f446ebc138ee4d36b44b8abdc6fd97ed
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244738B2

Reaction notes

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