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

HRID 2046032Notes

Reaction equation

HRID 2046032 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3bf10a0372c7416abe21267f7f985749
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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