Dimethylamine → 2-(4-(adamantan-1-yl)phenoxy)-N,N-dimethylacetamide

HRID 629514

반응식

HRID 629514 반응식
[C:1]12([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17](O)=[O:18])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:22][NH:23][CH3:24].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[C:1]12([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17]([N:23]([CH3:24])[CH3:22])=[O:18])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

참가 물질

8

반응물 5

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 625381PMID26882240-Compound-8HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 715420102-(4-(adamantan-1-yl)phenoxy)-N,N-dimethylacetamide수율 91.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of 2-(4-(adamantan-1-yl)phenoxy)acetic acid (0.2 g, 0.69 mmol), dimethylamine (0.031 g, 0.69 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide HCl (EDCI) (0.16 g, 0.83 mmol) and 1-hydroxybenzotriazole hydrate (HOBt) (0.11 g, 0.83 mmol) in N,N-dimethylformamide (2 mL) was added N,N-diisopropylethylamine (DIPEA) (0.106 mL, 1.74 mmol) and stirred at room temperature under nitrogen overnight. Reaction mixture was diluted with ethyl acetate and subsequentially washed with aqueous sodium hydroxide and brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was filtered and evaporated under reduced pressure to afford a crude solid, which was purified by silica gel column chromatography to give 2-(4-(adamantan-1-yl)phenoxy)-N,N-dimethylacetamide as a white solid (0.198 g, 90.3% yield).

후처리

  1. customReaction mixture
  2. washsubsequentially washed with aqueous sodium hydroxide and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationThe solvent was filtered
  5. customevaporated under reduced pressure
  6. customto afford a crude solid, which
  7. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-6fca86eeea9946a592fceecfd07c7e06
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315507B2

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