Acetic Acid → 2,2-dimethyl-N-(4-octylphenyl)-1,3-dioxan-5-amine

HRID 717616

반응식

HRID 717616 반응식
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:16][C:17]1([CH3:24])[O:22][CH2:21][C:20](=O)[CH2:19][O:18]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl.CCOCC>[CH3:16][C:17]1([CH3:24])[O:22][CH2:21][CH:20]([NH:13][C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:14]=2)[CH2:19][O:18]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 853464-OctylanilineHCID 27331412,2-Dimethyl-1,3-dioxan-5-oneHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 666148752,2-dimethyl-N-(4-octylphenyl)-1,3-dioxan-5-amine수율 63%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 3283Diethyl Ether용매

실험 절차

To a mixture of 4-n-octylaniline (0.205 g; 1 mmol) and 2,2-dimethyl-1,3-dioxan-5-one (Helvetica Chimica Acta, 2003, 86, 2467; 0.13 g; 1 mmol) and NaBH(OAc)3 in 1,2 dichloroethane (3.5 ml), AcOH (0.06 ml; 1 mmol) was added and the mixture was stirred for 2 h at room temperature under N2, diluted to 20 ml with Et2O and washed with 1N NaOH, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified crystallization from hexane to give the title compound (0.2 g; 63%) as a colourless solid. 1H-NMR (CDCl3) 6.97 (d, 2H, J=8.4 Hz); 6.54 (d, 2H, J=8.4 Hz); 4.1 (dd, broad s, 3H, J=4.2, 11.9 Hz); 3.74 (dd, 2H, J=4.2, 11.9 Hz); 3.4 (m, 1H); 2.47 (t, 2H, J=7.91 Hz); 1.55 (m, 2H+H2O); 1.46 (s, 3H); 1.43 (s, 3H); 1.25 (m, 10H); 0.86 (m, 3H).

후처리

  1. additionwas added
  2. washwashed with 1N NaOH, H2O, brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. customthe residue was purified
  7. customcrystallization from hexane

출처 및 근거

ORD 기록
ord-3e603cc5bb73451e8828880a2f85a777
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193716B2

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