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1,2-Dichloroethane → (+/-)2-Chloro-N-[2-methyl-2-(2-methyl-1-pyrrolidinyl)-1-phenylpropyl]-3-(trifluoromethyl)benzamide

HRID 20840
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HRID 20840 반응식
[CH3:1][C:2]([N:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[CH3:17])([CH3:11])[CH:3]([NH2:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:18][C:19]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:18][C:19]1[C:27]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([NH:10][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:2]([CH3:1])([N:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[CH3:17])[CH3:11])=[O:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27366772-Chloro-3-(trifluoromethyl)benzoic acidHCID 59347786[2-Methyl-2-(2-methyl-1-pyrrolidinyl)-1-phenylpropyl]amine

생성물 1

HCID 59347881(+/-)2-Chloro-N-[2-methyl-2-(2-methyl-1-pyrrolidinyl)-1-phenylpropyl]-3-(trifluoromethyl)benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of [2-methyl-2-(2-methyl-1-pyrrolidinyl)-1-phenylpropyl]amine D26 (0.150 g; 0.647 mmol), 2-chloro-3-(trifluoromethyl)benzoic acid (0.174 g; 0.775 mmol), EDC (0.149 g; 0.777 mmol) and HOBt (0.020 g; 0.148 mmol) in DCM (4 ml) was shaken at room temperature for 66 hours. Saturated sodium hydrogen carbonate (8 ml) was added and shaking continued for 0.5 hours. The organic layer was passed through a phase separation cartridge and applied to a 2 g SCX column. The column was washed with DCM and methanol and the product eluted with 1M ammonia in methanol. The crude product was purified by chromatography on silica gel (20 g) eluting with 0-100% ethyl acetate in pentane gradient to afford the title compound as two pairs of enantiomers.

후처리

  1. stirringshaking
  2. waitcontinued for 0.5 hours
  3. customThe organic layer was passed through a phase separation cartridge
  4. washThe column was washed with DCM and methanol
  5. washthe product eluted with 1M ammonia in methanol
  6. customThe crude product was purified by chromatography on silica gel (20 g)
  7. washeluting with 0-100% ethyl acetate in pentane gradient

출처 및 근거

ORD 기록
ord-d442d140b910474784016bfda8a268a9
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745642B2

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