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

HRID 860763

반응식

HRID 860763 반응식
[O:1]1[CH2:14][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[CH3:15][NH:16][CH3:17]>CO.CN(C=O)C>[OH:1][CH:2]([CH2:14][N:16]([CH3:17])[CH3:15])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1

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 887Methanol용매2회HCID 6228Dimethylformamide용매

실험 절차

4-(2,3-Epoxypropoxy)nitrobenzene (obtained as described in Synthetic Communications, 1994, 24, 833; 4.3 g,) was dissolved in methanol (30 ml) and DMF (10 ml). A solution of dimethylamine in methanol (2M, 17 ml) was added and the mixture was stirred overnight. Volatile material was removed by evaporation and the residue was partitioned between saturated sodium bicarbonate (100 ml) and ethyl acetate (100 ml). The organic layer was separated and washed with saturated sodium chloride (2×100 ml) and dried (MgSO4). Concentration gave the product as an oil that slowly crystallised under high vacuum (4.79 g, 89.9%). NMR (CDCl3): 2.33 (s, 6H), 2.98 (m, 1H), 2.54 (m, 1H), 4.00 (m, 3H), 7.00 (d, 2H), 8.20 (d, 2H); MS (M+H)+: 241.

후처리

  1. customVolatile material was removed by evaporation
  2. customthe residue was partitioned between saturated sodium bicarbonate (100 ml) and ethyl acetate (100 ml)
  3. customThe organic layer was separated
  4. washwashed with saturated sodium chloride (2×100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationConcentration

출처 및 근거

ORD 기록
ord-1b5988d156b64a06bc51689a4f0e14cb
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153964B2

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