(R)-1-(3-Ethoxyphenyl)ethanamine hydrochloride → [4-[(1S,3R/S)-3-[[(1R)-1-(3-ethoxyphenyl)ethyl]amino]cyclopentyl]-phenyl]morpholino-methanone

HRID 1614875Notes

Reaction equation

HRID 1614875 reaction equation
[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:19][CH2:18][C:17](=O)[CH2:16]3)=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl.[CH2:22]([O:24][C:25]1[CH:26]=[C:27]([C@H:31]([NH2:33])[CH3:32])[CH:28]=[CH:29][CH:30]=1)[CH3:23]>>[CH2:22]([O:24][C:25]1[CH:26]=[C:27]([C@H:31]([NH:33][CH:17]2[CH2:18][CH2:19][C@H:15]([C:12]3[CH:13]=[CH:14][C:9]([C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:8])=[CH:10][CH:11]=3)[CH2:16]2)[CH3:32])[CH:28]=[CH:29][CH:30]=1)[CH3:23]

Participants

3

Reactant 2

HCID 44828801(R)-1-(3-Ethoxyphenyl)ethanamine hydrochlorideHCID 49833947(3s)-3-[4-(Morpholine-4-carbonyl)phenyl]-cyclopentanone

Product 1

HCID 69901320[4-[(1S,3R/S)-3-[[(1R)-1-(3-ethoxyphenyl)ethyl]amino]cyclopentyl]-phenyl]morpholino-methanone

Procedure

General procedure B was followed using (3S)-3-[4-(Morpholine-4-carbonyl)phenyl]-cyclopentanone (preparation 15) as the ketone and (1R)-1-(3-ethoxyphenyl)-ethanamine hydrochloride as the amine. 1H NMR (600 MHz, DMSO) δ 7.33-7.21 (m, 4H), 7.19 (t, J=7.8 Hz, 1H), 6.93-6.86 (m, 2H), 6.74 (dd, J=7.9, 2.3 Hz, 1H), 4.00 (q, J=7.0 Hz, 2H), 3.70 (q, J=6.6 Hz, 1H), 3.57 (br s, 4H), 3.33 (br s, 4H), 3.27-3.20 (m, 1H), 3.03 (t, J=8.3 Hz, 1H), 2.11-2.03 (m, 1H), 1.95-1.88 (m, 1H), 1.78-1.72 (m, 1H), 1.64-1.41 (m, 3H), 1.34-1.28 (m, 3H), 1.23 (d, J=6.6 Hz, 3H).

Sources & evidence

ORD record
ord-1684e7bb632a44b79b7082bc47c9e44a
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

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