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Triethylamine → N-[[1-(Dimethylamino)cyclopentyl](phenyl)methyl]-2,6-dimethyl benzamide

HRID 20832
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HRID 20832 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4](Cl)=[O:5].[NH2:12][CH:13]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:14]1([N:19]([CH3:21])[CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15]1.ClC1C(C(F)(F)F)=CC=CC=1C(NC(C1(N(C)C)CCCC1)C1C=CC=CC=1)=O.C(N(CC)CC)C>C(Cl)Cl>[CH3:20][N:19]([CH3:21])[C:14]1([CH:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[NH:12][C:4](=[O:5])[C:3]2[C:2]([CH3:1])=[CH:10][CH:9]=[CH:8][C:7]=2[CH3:11])[CH2:18][CH2:17][CH2:16][CH2:15]1
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 890962,6-Dimethylbenzoyl chlorideHCID 11521393{1-[Amino(phenyl)methyl]cyclopentyl}dimethylamineHCID 116115852-Chloro-N-[[1-(dimethylamino)cyclopentyl](phenyl)methyl]-3-(trifluoromethyl)benzamide

생성물 1

HCID 11624468N-[[1-(Dimethylamino)cyclopentyl](phenyl)methyl]-2,6-dimethyl benzamide수율 97%

시약·촉매·용매

1
HCID 6344Dichloromethane용매2회

실험 절차

A solution of 2,6-dimethylbenzoyl chloride (1.7 g, 10.1 mmol) in DCM (10 ml) was added dropwise to a mixture of {1-[amino(phenyl)methyl]cyclopentyl}dimethylamine D3 enantiomer 2 (2.0 g, 9.2 mmol), and triethylamine (1.4 ml, 10.0 mmol) in DCM (40 ml) and stirred at room temperature for 2 h. The mixture was washed with saturated aqueous sodium hydrogen carbonate, the organic layer was separated through a phase separation cartridge and then evaporated to a white solid. Chromatography with eluent 50-100% ethyl acetate/pentane, then 0-10% methanol/ethyl acetate afforded the title product as a white solid (3.1 g, 97%). 1H NMR (CDCl3) δ: 0.85-1.00 (1H, m), 1.30-1.55 (3H, m), 1.60-1.75 (2H, m), 1.78-1.90 (2H, m), 2.21 (6H, s), 2.31 (6H, s), 5.19 (1H, d, J=6 Hz), 6.79 (1H, br d), 7.02 (2H, d, J=8 Hz), 7.16 (1H, t, J=8 Hz), 7.20-7.35 (3H, m), 7.43 (2H, m). Mass Spectrum (Electrospray LC/MS): Found 351 (MH+). C23H30N2O requires 350. Ret. time 2.0 min. The white solid product was converted to the HCl salt using 1M HCl/diethylether to afford the salt as a white solid on evaporation.

후처리

  1. washThe mixture was washed with saturated aqueous sodium hydrogen carbonate
  2. customthe organic layer was separated through a phase separation cartridge
  3. customevaporated to a white solid

출처 및 근거

ORD 기록
ord-4d7c4d063740466689760c3e4bbd4003
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745642B2

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