Dimethylamine → 1-(Dimethylamino)-3-(4-nitrophenoxy)propan-2-ol

HRID 433922

반응식

HRID 433922 반응식
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]2[O:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:15][NH:16][CH3:17]>CO.CN(C=O)C>[CH3:15][N:16]([CH2:11][CH:10]([OH:12])[CH2:9][O:8][C:7]1[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:17]

참가 물질

5

반응물 2

HCID 674DimethylamineHCID 213272-((4-Nitrophenoxy)methyl)oxirane

생성물 1

HCID 31320441-(Dimethylamino)-3-(4-nitrophenoxy)propan-2-ol

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

1-(4-Nitrophenoxy)-2,3-epoxypropane (Reference Example 1-B, 4.3 g) was dissolved in methanol (30 ml) and DMF (10 ml). Dimethylamine (2M solution in methanol, 17 ml) was added and the mixture was stirred at ambient temperature overnight. The reaction mixture was evaporated to dryness and the residue was dissolved in saturated sodium bicarbonate solution and ethyl acetate. The ethyl acetate layer was separated and washed twice with saturated brine, dried over anhydrous sodium sulphate, filtered and evaporated to yield an oil that slowly crystallised under high vacuum (4.79 g, 89.9%). NMR: (CDCl3, 300 MHz) 2.33 (s, 6H), 2.98 (m, 1H), 2.54 (m, 1H), 4.00 (m,3 H), 7.00 (d, 2H), 8.20 (d, 2H); M.S.: (ES+) 241 (MH+).

후처리

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in saturated sodium bicarbonate solution
  3. customThe ethyl acetate layer was separated
  4. washwashed twice with saturated brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto yield an oil that
  9. customslowly crystallised under high vacuum (4.79 g, 89.9%)

출처 및 근거

ORD 기록
ord-509b8155b009482dbfc7f082a7050417
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670368B1

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