Hydrochloric Acid → Rac-1-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-piperidine-3-carboxylic acid

HRID 556463

반응식

HRID 556463 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([OH:9])=[O:8])[CH2:2]1.[OH-].[Na+].Br[C:13]1([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=2)[C:21]2[C:16](=[CH:17][C:18]([Cl:22])=[CH:19][CH:20]=2)[NH:15][C:14]1=[O:23].Cl>O.O1CCOCC1>[Cl:22][C:18]1[CH:17]=[C:16]2[C:21]([C:13]([N:1]3[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([OH:9])=[O:8])[CH2:2]3)([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)[C:14](=[O:23])[NH:15]2)=[CH:20][CH:19]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 4498Nipecotic AcidHCID 14798Sodium HydroxideHCID 575072733-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

생성물 1

HCID 24950102Rac-1-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-piperidine-3-carboxylic acid

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

To the mixture of piperidine-3-carboxylic acid (600 mg, 4.5 mmol) and NaOH (360 mg, 9 mmol) in water (5 mL) and dioxane (5 mL) was added rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (1.1 g, 3 mmol). The mixture was stirred at room temperature for 1 h and then diluted by water (30 mL). The resulting solution was neutralized to pH=7 with hydrochloride acid and extracted by dichloromethane. The organic phase was dried over Na2SO4, filtered and concentrated to give rac-1-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-3-carboxylic acid yield: (0.9 g, 71%). MS: [M−H]−=417.

후처리

  1. extractionextracted by dichloromethane
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e5c6687063234747b2d042bc19b05881
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058269B2

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