Hydrochloric Acid → 1-Cyclohexyl-3-[2,4-dichloro-4'-(3-dimethylamino-propoxy)-biphenyl-3-ylmethyl]-pyrrolidin-2-one hydrochloride

HRID 2235322Notes

Reaction equation

HRID 2235322 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([Cl:28])=[C:10]([C:24]([Cl:27])=[CH:25][CH:26]=2)[CH2:11][CH:12]2[CH2:16][CH2:15][N:14]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:13]2=[O:23])=[CH:4][CH:3]=1.[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Br[CH2:39][CH2:40][CH2:41][N:42]([CH3:44])[CH3:43].Cl>CC(C)=O.C(Cl)Cl.CCOCC>[ClH:27].[CH:17]1([N:14]2[CH2:15][CH2:16][CH:12]([CH2:11][C:10]3[C:9]([Cl:28])=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([O:1][CH2:39][CH2:40][CH2:41][N:42]([CH3:44])[CH3:43])=[CH:3][CH:4]=4)[CH:26]=[CH:25][C:24]=3[Cl:27])[C:13]2=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 12440776(3-Bromo-propyl)-dimethyl-amine hydrochlorideHCID 592993283-(3-(4-Hydroxyphenyl)-2,6-dichlorobenzyl)-1-cyclohexylpyrrolidin-2-one

Product 1

HCID 684719151-Cyclohexyl-3-[2,4-dichloro-4'-(3-dimethylamino-propoxy)-biphenyl-3-ylmethyl]-pyrrolidin-2-one hydrochlorideYield 65.1%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Place 3-(3-(4-hydroxyphenyl)-2,6-dichlorobenzyl)-1-cyclohexylpyrrolidin-2-one (0.200 g, 0.478 mmol), sodium iodide (0.072 g, 0.478 mmol, and cesium carbonate (1.25 g, 3.82 mmol) in acetone (lOmL). Add 3-bromo-N,N-dimethylpropan-1-amine hydrochloride (0.194 g, 0.956 mmol) and stir at room temperature for 3 hours. Add water and extract with DCM. Dry, filter, and concentrate. Purify by silica gel to give the free base. Dissolve in DCM and add 2M HCl in ether. Concentrate to give 84 mg (33%) of the title compound as a tan solid. Mass spectrum (apci) m/z=503.3 (M+H).

Workup

  1. extractionAdd water and extract with DCM
  2. customDry
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify by silica gel
  6. customto give the free base
  7. concentrationConcentrate

Sources & evidence

ORD record
ord-5b70c7b2402747c89b2d1b7cd14da646
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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