4-Aminophenethyl alcohol → HCID 118037227, compound

HRID 1508975Notes

Reaction equation

HRID 1508975 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH2:12][CH2:11][CH2:10][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>>[ClH:1].[C:8]1([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)[CH2:12][CH2:11][CH2:10][CH:9]=1

Participants

3

Reactant 2

HCID 669044-Aminophenethyl alcoholHCID 90338499HCID 90338499, compound

Product 1

HCID 118037227HCID 118037227, compoundYield 79%

Procedure

Following general procedure B1, 4-chloro-2-(cyclopent-1-en-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine (0.095 g, 0.43 mmol) was reacted with 2-(4-aminophenyl)ethanol (0.089 g, 0.65 mmol), followed by formation of the hydrochloride salt to afford the title compound (0.110 g, 79%) as a yellow solid. MW=356.89. 1H NMR (DMSO-d6, 500 MHz) δ 13.67 (s, 1H), 9.71 (s, 1H), 7.33 (d, J=8.5 Hz, 2H), 7.26 (d, J=8.5 Hz, 2H), 6.99 (s, 1H), 6.66 (s, 1H), 3.64 (t, J=7.0 Hz, 2H), 3.13 (t, J=7.5 Hz, 2H), 2.84 (t, J=7.5 Hz, 2H), 2.76 (t, J=7.0 Hz, 2H), 2.56 (t, J=7.5 Hz, 4H), 2.18 (quin, J=7.5 Hz, 2H) 1.94 (quin, J=7.5 Hz, 2H); APCI MS m/z 321 [M+H]+.

Sources & evidence

ORD record
ord-db35cbe7abdb49aeb201000158943d27
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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