Benzylamine → N-benzyl(2,2-dimethyl-1,3-dioxan-5-yl)methanamine

HRID 533197Notes

Reaction equation

HRID 533197 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9][CH2:8]1)(=O)=O.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)(=O)C>[CH2:15]([NH:22][CH2:6][CH:7]1[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9][CH2:8]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 10998661(2,2-Dimethyl-1,3-dioxan-5-yl)methyl methanesulfonate

Product 1

HCID 25223589N-benzyl(2,2-dimethyl-1,3-dioxan-5-yl)methanamineYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2,2-dimethyl-1,3-dioxan-5-yl)methyl methanesulfonate (1.70 g, 7.58 mmol) in benzylamine (10 mL, 92 mmol) was stirred at 80° C. and monitored by TLC. After 2 h the reaction was complete therefore concentrated in vacuo. The residue was diluted with toluene (containing a small amount of ethyl acetate) and washed with water, dried and concentrate in vacuo. Column chromatography on silica eluting with ethyl acetate afforded N-benzyl(2,2-dimethyl-1,3-dioxan-5-yl)methanamine (1.51 g, 85% yield) as a yellow oil. 13C NMR (CD3OD) δ 140.8, 129.4 (2XCH), 128.1, 99.3, 64.0 (2XCH2), 54.7, 33.7, 25.6, 23.0

Workup

  1. concentrationAfter 2 h the reaction was complete therefore concentrated in vacuo
  2. additionThe residue was diluted with toluene (
  3. additioncontaining a small amount of ethyl acetate) and
  4. washwashed with water
  5. customdried
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-381e66c3d44e480c8b3aaf16c69869b2
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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