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

HRID 2235322ノート

反応式

HRID 2235322 の反応式
[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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5b70c7b2402747c89b2d1b7cd14da646
出典データセット
uspto-grants-2010_05
特許番号
US07713979B2

反応ノート

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