4'-Hydroxypropiophenone → Dibutyl-{3-[4-(3,8-dimethyl-imidazo[1,2-a]pyridin-2-yl)-phenoxy]-propyl}-amine

HRID 4728

Reaction equation

HRID 4728 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH3:10])=[CH:4][CH:3]=1.Br[CH2:13][CH2:14][CH2:15]Cl.BrBr.[CH3:19][C:20]1[C:21]([NH2:26])=[N:22][CH:23]=[CH:24][CH:25]=1.[CH2:27]([NH:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH3:30]>>[CH2:27]([N:31]([CH2:13][CH2:14][CH2:15][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:26]=[C:21]3[C:20]([CH3:19])=[CH:25][CH:24]=[CH:23][N:22]3[C:9]=2[CH3:10])=[CH:4][CH:3]=1)[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 5

HCID 62714'-HydroxypropiophenoneHCID 80061-Bromo-3-chloropropaneHCID 8148DibutylamineHCID 153472-Amino-3-methylpyridineHCID 24408Bromine

Product 1

HCID 10179589Dibutyl-{3-[4-(3,8-dimethyl-imidazo[1,2-a]pyridin-2-yl)-phenoxy]-propyl}-amineYield 62%

Procedure

p-Hydroxypropiophenone (50 g, 0.33 mmol) was reacted with 1-bromo-3-chloropropane and the resulting compound reacted with bromine as described in Example 1. The resulting compound was reacted with 3-methyl-2-aminopyridine (1.7 g, 16 mmol) and the product reacted with dibutylamine as described in Example 1 to produce 2.4 g. (62% yield) of the title compound as the HCl salt, mp 202° C. to 204° C. IR(KBr): 3420, 2620, 1650 1605cm-1. MS: 408 (M+). 1H NMR (CD3OD): δ8.58 (d, J=6.5 Hz, 1H), 7.85-7.71 (m, 3H), 7.48 (t, J=6.7 Hz, 1H), 7.22 (d, J=8.7 Hz, 2H), 4.26 (t, J=5.8 Hz, 2H), 3.52-3.16 (m, 6H), 2.75 (s, 3H), 2.73 (s, 3H), 2.33 (m, 2H), 1.87-1.36 (m, 8H), 1.02 (m, 6H).

Workup

  1. customto produce 2.4 g

Sources & evidence

ORD record
ord-9efe203deaa442a39739846cd4aff0b2
Source dataset
uspto-grants-1988_02
Patent number
US04727145

Linked notes

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