4-Aminophenethyl alcohol → HCID 90338659, compound

HRID 1508966Notes

Reaction equation

HRID 1508966 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[N:5]=[C:4]2[CH2:13][CH2:14][CH2:15][C:3]=12.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][OH:25])=[CH:19][CH:18]=1>>[S:10]1[CH:11]=[CH:12][C:8]([C:6]2[N:5]=[C:4]3[CH2:13][CH2:14][CH2:15][C:3]3=[C:2]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][OH:25])=[CH:19][CH:18]=3)[CH:7]=2)=[CH:9]1

Participants

3

Reactant 2

HCID 669044-Aminophenethyl alcoholHCID 90338658HCID 90338658, compound

Product 1

HCID 90338659HCID 90338659, compoundYield 29.7%

Procedure

Following general procedure B1, 4-chloro-2-(thiophen-3-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine (0.060 g, 0.25 mmol) was reacted with 2-(4-aminophenyl)ethanol (0.041 g, 0.30 mmol), followed by formation of the hydrochloride salt to afford the title compound (0.025 g, 27%) as a white solid. MW=356.85. MW=372.91. 1H NMR (DMSO-d6, 500 MHz) δ 13.91 (s, 1H), 9.68 (s, 1H), 8.37-8.32 (m, 1H), 7.80-7.76 (m, 1H), 7.59-7.55 (m, 1H), 7.34 (d, J=8.5 Hz, 2H), 7.30 (d, J=8.5 Hz, 2H), 7.03 (s, 1H), 4.67 (s, 1H), 3.65 (t, J=7.0 Hz, 2H), 3.15 (t, J=7.5 Hz, 2H), 2.88 (t, J=7.0 Hz, 2H), 2.77 (t, J=7.0 Hz, 2H), 2.20 (quin, J=7.5 Hz, 2H); APCI MS m/z 337 [M+H]+.

Sources & evidence

ORD record
ord-301518a012134d6e86b1b1b447ec870d
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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