Ammonia → [(2,2-Dimethyl-1,3-dioxan-5-yl)methyl](methyl)amine

HRID 533199Notes

Reaction equation

HRID 533199 reaction equation
[CH3:1][NH2:2].CS(O[CH2:8][CH:9]1[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11][CH2:10]1)(=O)=O.C(Cl)Cl.N>CS(C)=O.C(Cl)(Cl)Cl.CO.C(Cl)Cl>[CH3:15][C:12]1([CH3:16])[O:13][CH2:14][CH:9]([CH2:8][NH:2][CH3:1])[CH2:10][O:11]1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 6329MethylamineHCID 6344DichloromethaneHCID 10998661(2,2-Dimethyl-1,3-dioxan-5-yl)methyl methanesulfonate

Product 1

HCID 25223587[(2,2-Dimethyl-1,3-dioxan-5-yl)methyl](methyl)amineYield 52%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolventHCID 21226129Dichloromethane methanolSolvent2×

Conditions

Temperature
75 °C

Procedure

Methylamine solution (3 mL, 34.8 mmol) was added to a solution of (2,2-dimethyl-1,3-dioxan-5-yl)methyl methanesulfonate (0.9 g, 4.01 mmol, prepared as per B. Xu et al. J. Med. Chem. 2002, 45, 5694) in DMSO (7 mL) and stirred at 75° C. overnight. The reaction was diluted with CHCl3 and the CHCl3 washed with water (×2), dried and concentrated in vacuo to afford approximately 670 mg of crude product. The crude material was columned on silica eluting with DCM, 20% MeOH/DCM, and 20% 7N NH3 in MeOH/DCM to afford (2,2-dimethyl-1,3-dioxan-5-yl)-N-methylmethanamine (330 mg, 52% yield) as an oily residue. 13C NMR (CD3OD) δ 99.7, 64.4 (2×CH2), 52.3, 36.9, 36.0, 26.0, 23.5.

Workup

  1. washthe CHCl3 washed with water (×2)
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customto afford approximately 670 mg of crude product

Sources & evidence

ORD record
ord-6b9b32dc1d5c4353ab26101d932e4a93
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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