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

HRID 1614876Notes

Reaction equation

HRID 1614876 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:21][C:22]1[CH:23]=[C:24]([C@H:28]([NH2:30])[CH3:29])[CH:25]=[CH:26][CH:27]=1>>[Cl:21][C:22]1[CH:23]=[C:24]([C@H:28]([NH:30][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)[CH3:29])[CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 2507697(R)-1-(3-chlorophenyl)ethanamineHCID 49833947(3s)-3-[4-(Morpholine-4-carbonyl)phenyl]-cyclopentanone

Product 1

HCID 69901851[4-[(1S,3R/S)-3-[[(1R)-1-(3-chlorophenyl)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 (R)-1-(3-chlorophenyl)ethanamine as the amine. 1H NMR (600 MHz, DMSO) δ 7.44-7.42 (m, 1H), 7.35-7.22 (m, 7H), 3.76 (q, J=6.6 Hz, 1H), 3.57 (br m, 4H), 3.33 (br m, 4H), 3.27-3.19 (m, 1H), 3.02 (m, 1H), 2.07 (m, 1H), 1.93 (m, 1H), 1.77-1.41 (m, 4H), 1.23 (d, J=5.3 Hz, 3H).

Sources & evidence

ORD record
ord-69fb9fecbbda490bbee755249c1b6f6f
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

Loading…