Triethylamine → {(3RS,4SR)-3-(3,4-Dichloro-phenyl)-4-[(RS)-1-(4-trifluoromethyl-phenoxy)-ethyl]pyrrolidin-1-yl}-[4-(2-dimethylamino-ethyl)-piperazin-1-yl]-methanone

HRID 1158660Notes

Reaction equation

HRID 1158660 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([CH:14]([O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[CH3:15])[CH2:12][N:11]([C:27](Cl)=[O:28])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].CCN(CC)CC.[CH3:37][N:38]([CH3:47])[CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([CH:14]([O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=3)[CH3:15])[CH2:12][N:11]([C:27]([N:44]3[CH2:45][CH2:46][N:41]([CH2:40][CH2:39][N:38]([CH3:47])[CH3:37])[CH2:42][CH2:43]3)=[O:28])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27362291-(2-(Dimethylamino)ethyl)piperazineHCID 86628179(3RS,4SR)-3-(3,4-Dichloro-phenyl)-4-[(RS)-1-(4-trifluoromethyl-phenoxy)-ethyl]-pyrrolidine-1-carbonyl chloride

Product 1

HCID 67327778{(3RS,4SR)-3-(3,4-Dichloro-phenyl)-4-[(RS)-1-(4-trifluoromethyl-phenoxy)-ethyl]pyrrolidin-1-yl}-[4-(2-dimethylamino-ethyl)-piperazin-1-yl]-methanoneYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3RS,4SR)-3-(3,4-dichloro-phenyl)-4-[(RS)-1-(4-trifluoromethyl-phenoxy)-ethyl]-pyrrolidine-1-carbonyl chloride (58 mg, 0.12 mmol) in CH2Cl2 (2 ml) were added Et3N (0.02 mL, 0.15 mmol) and dimethyl-(2-piperazin-1-yl-ethyl)-amine (0.03 mL) (commercially available). Stirring was continued overnight, and the reaction mixture was concentrated under vacuo and directly purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH3, 9/4/1) to yield 46 mg (63%) of the title compound as light yellow oil. ES-MS m/e: 587.3 (M+H+).

Workup

  1. concentrationthe reaction mixture was concentrated under vacuo
  2. customdirectly purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH3, 9/4/1)

Sources & evidence

ORD record
ord-76df5185f20f4affb2325e19b24146de
Source dataset
uspto-grants-2010_10
Patent number
US07812021B2

Reaction notes

Loading…