4-(4-Chlorophenyl)-4-hydroxypiperidine → HCID 58280468, compound

HRID 1879493Notes

Reaction equation

HRID 1879493 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][N:9]([CH2:20][C:21]2[CH:22]=[C:23]([CH:35]=[CH:36][CH:37]=2)[CH2:24][N:25]2[CH:29]([C:30](O)=[O:31])[CH2:28][CH2:27][S:26]2(=[O:34])=[O:33])[C@H:10]([CH2:16][N:17]([CH3:19])[CH3:18])[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:6]([F:38])[C:5]([O:39][CH3:40])=[CH:4][CH:3]=1.[Cl:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2([OH:54])[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]2)=[CH:44][CH:43]=1>>[Cl:1][C:2]1[C:7]([CH2:8][N:9]([CH2:20][C:21]2[CH:22]=[C:23]([CH:35]=[CH:36][CH:37]=2)[CH2:24][N:25]2[CH:29]([C:30]([N:51]3[CH2:50][CH2:49][C:48]([C:45]4[CH:46]=[CH:47][C:42]([Cl:41])=[CH:43][CH:44]=4)([OH:54])[CH2:53][CH2:52]3)=[O:31])[CH2:28][CH2:27][S:26]2(=[O:34])=[O:33])[C@H:10]([CH2:16][N:17]([CH3:18])[CH3:19])[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:6]([F:38])[C:5]([O:39][CH3:40])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 58280450HCID 58280450, compound2×

Product 1

HCID 58280468HCID 58280468, compoundYield 62%

Procedure

2-(3-{[(6-Chloro-2-fluoro-3-methoxy-benzyl)-((S)-1 dimethylaminomethyl-3,3-dimethyl-butyl)-amino]-methyl}-benzyl)-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid (Intermediate 7, 0.081 g, 0.135 mmol) was reacted with 4-(4-chlorophenyl)-4-hydroxypiperidine (available from Aldrich Chemical Company, Inc., 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233, USA; 0.035, 0.166 mmol) to form [2-(3-{[(6-Chloro-2-fluoro-3-methoxy-benzyl)-((S)-1-dimethylaminomethyl-3,3-dimethyl-butyl)-amino]-methyl}-benzyl)-1,1-dioxo-1λ6-isothiazolidin-3-yl]-[4-(4-chloro-phenyl)-4-hydroxy-piperidin-1-yl]-methanone (0.066 g, 62%). m/z=791 (M+1); HRMS: calcd for C40H54Cl2FN4O5S. Calc [M+H+] 791.3171. found 791.3169.

Sources & evidence

ORD record
ord-86ddbe30cbeb4c47b681399586f4e3df
Source dataset
uspto-grants-2012_11
Patent number
US08314250B2

Reaction notes

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