Formaldehyde → HCID 67323666, compound

HRID 1397313Notes

Reaction equation

HRID 1397313 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:12]3([CH2:18][NH2:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[C:22](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:22][NH:19][CH2:18][C:12]1([C:9]2[S:10][CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67322930(4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine

Product 1

HCID 67323666HCID 67323666, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

(4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine (300 mg, 1.1 mmol) was dissolved in 1,2-dichloroethane (30 mL) and cooled to 0° C. Formaline solution (˜0.1 mL, 35%) was added to the solution, followed by sodiumtriacetoxy borohydride (0.16 g, 0.76 mmol). The reaction mixture was further stirred for 45 min maintaining the same temperature. The reaction mixture was then quenched with 10% NaHCO3 solution and diluted with CH2Cl2. The organic layer was separated, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography (silica 60-120 mesh, eluent 10-20% MeOH in CHCl3) to afford N-methyl-1-(4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine (120 mg, yield 38%). 1H NMR (300 MHz, CDCl3) δ 7.90-7.88 (m, 2H), 7.48 (s, 1H), 7.44-7.34 (m, 3H), 3.93-3.86 (m, 2H), 3.75-3.67 (ddd, J=12.0 Hz, 8.9 Hz, 3.0 Hz, 2H), 3.01 (s, 2H), 2.49 (s, 3H), 2.36-2.39 (m, 2H), 2.09-2.01 (m, 2H). MS (ESI) m/z: Calculated for C16H20N2OS: 288.13. found: 289.2 (M+H)+.

Workup

  1. temperaturemaintaining the same temperature
  2. customThe reaction mixture was then quenched with 10% NaHCO3 solution
  3. additiondiluted with CH2Cl2
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica 60-120 mesh, eluent 10-20% MeOH in CHCl3)

Sources & evidence

ORD record
ord-c61d9966218b438694bdaf96a4bd0576
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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