(R)-1-(4-Fluoro-3-methoxyphenyl)ethanamine hydrochloride → (1r/s,3r)-n-[(1r)-1-(4-Fluoro-3-methoxy-phenyl)ethyl]-3-[4-(2-morpholinosulfonylethyl)phenyl]cyclopentanamine

HRID 1614873Notes

Reaction equation

HRID 1614873 reaction equation
[N:1]1([S:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C@@H:18]3[CH2:22][CH2:21][C:20](=O)[CH2:19]3)=[CH:14][CH:13]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl.[F:25][C:26]1[CH:31]=[CH:30][C:29]([C@H:32]([NH2:34])[CH3:33])=[CH:28][C:27]=1[O:35][CH3:36]>>[F:25][C:26]1[CH:31]=[CH:30][C:29]([C@H:32]([NH:34][CH:20]2[CH2:21][CH2:22][C@@H:18]([C:15]3[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][S:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)(=[O:9])=[O:8])=[CH:17][CH:16]=3)[CH2:19]2)[CH3:33])=[CH:28][C:27]=1[O:35][CH3:36]

Participants

3

Reactant 2

HCID 53484667(R)-1-(4-Fluoro-3-methoxyphenyl)ethanamine hydrochlorideHCID 68751067(3R)-3-{4-[2-(Morpholine-4-sulfonyl)-ethyl]-phenyl}-cyclopentanone

Product 1

HCID 68093342(1r/s,3r)-n-[(1r)-1-(4-Fluoro-3-methoxy-phenyl)ethyl]-3-[4-(2-morpholinosulfonylethyl)phenyl]cyclopentanamine

Procedure

General procedure B was followed using (3R)-3-{4-[2-(morpholine-4-sulfonyl)-ethyl]-phenyl}-cyclopentanone (preparation 49) as the ketone and (1R)-1-(4-fluoro-3-methoxyphenyl)ethylamine hydrochloride as the amine. 1H NMR (300 MHz, DMSO) δ 7.23-7.04 (m, 6H), 6.92-6.83 (m, 1H), 3.82 (s, 3H), 3.80-3.68 (m, 1H), 3.66-3.55 (m, 4H), 3.37-3.26 (m, 2H), 3.22-3.10 (m, 4H), 3.06-2.78 (m, 4H), 2.20-1.13 (m, 6H), 1.23 (d, J=6.6 Hz, 3H).

Sources & evidence

ORD record
ord-5cd45f48cfac47fa94cd6140036aae6e
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

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