4-Aminophenethyl alcohol → HCID 118037275, compound

HRID 1508835Notes

Reaction equation

HRID 1508835 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=2)[N:6]=[C:5]2[CH2:17][CH2:18][CH2:19][C:4]=12.[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([CH2:25][CH2:26][OH:27])=[CH:23][CH:22]=1>>[ClH:2].[Cl:16][C:11]1[CH:10]=[C:9]([C:7]2[N:6]=[C:5]3[CH2:17][CH2:18][CH2:19][C:4]3=[C:3]([NH:20][C:21]3[CH:29]=[CH:28][C:24]([CH2:25][CH2:26][OH:27])=[CH:23][CH:22]=3)[CH:8]=2)[CH:14]=[C:13]([Cl:15])[CH:12]=1

Participants

3

Reactant 2

HCID 669044-Aminophenethyl alcoholHCID 118036999HCID 118036999, compound

Product 1

HCID 118037275HCID 118037275, compoundYield 65%

Procedure

Following General Procedure A1, 4-chloro-2-(3,5-dichlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine hydrochloride (0.100 g, 0.33 mmol) was reacted with 4-aminophenethyl alcohol (0.055 g, 0.40 mmol), followed by the formation of the hydrochloride salt to afford the title compound (0.065 g, 65%) as a light yellow solid. MW=435.77. 1H NMR (DMSO-d6, 300 MHz) δ 14.15 (s, 1H), 9.69 (s, 1H), 7.88 (d, J=1.8 Hz, 2H), 7.87-7.83 (m, 1H), 7.33 (s, 4H), 7.07 (s, 1H), 3.64 (t, J=6.9, 2H), 3.13 (t, J=7.6 Hz, 2H), 2.92 (t, J=7.6 Hz, 2H), 2.76 (t, J=6.9 Hz, 2H), 2.28-2.17 (m, 2H); APCI MS m/z 399 [M+H]+.

Sources & evidence

ORD record
ord-892c5986805a4104bf654ac260c99b9b
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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